00:00:00 Is that the same notepad you used before?

00:00:07 No. I had cards before, but Robert decided that I should look more professional by using a notepad.

00:00:15 Koji, I know that you were born in Hong Kong on May 11, 1925, but I know very little else about your family and your growing up.

00:00:28 Maybe you could tell me a little bit about how you came to be in Hong Kong in the first place.

00:00:33 I don't know. That has nothing to do with it. I was not born there.

00:00:38 My father was in the banking business, which is now called the Bank of Tokyo.

00:00:44 They are sent to many countries. He happened to be in Hong Kong, and then I was born there.

00:00:52 The next assignment was Lyon, then London, and then Alexandria.

00:01:00 As a result, I was born in Hong Kong, then went to Lyon, stayed there for three or four years,

00:01:06 then London for three or four years, and then Alexandria for three or four years.

00:01:10 Then I came back. My parents came back to Japan the first time when I was about 13 or 14 years old.

00:01:18 Then I started learning Japanese. That's the way it was.

00:01:21 Did the family speak Japanese before you came back to Japan?

00:01:24 Oh, yeah. Most of the winners, like all young kids, are when you speak with your brothers.

00:01:31 I'm the eldest, and a brother in each city – Lyon, London, Alexandria.

00:01:38 We spoke, I think, probably in French.

00:01:44 Not probably. It is in French, because Alexandria was the last city, and that was still a very strong French influence.

00:01:52 I think French and English mixed, I think. That's what we were speaking, with my parents' Japanese.

00:01:59 Your schooling, particularly in Alexandria, was done in French?

00:02:04 No. This was called the British Boys' School, and it still exists, this school.

00:02:11 It's interesting. There are two chemists which came out from this school.

00:02:15 One is a Canadian well-known carbohydrate chemist, Steve Hinesian,

00:02:20 and the other one is a professor at the Australian National University in Canberra, Amarego.

00:02:25 He's sort of a physical, organic, heterocyclic. He's written a book.

00:02:29 Then I recently found out – these are a little younger than my age, okay?

00:02:36 I only knew the name of one classmate at this British Boys' School in Alexandria.

00:02:44 His name was Alec Kitroev, and that's the only name I knew.

00:02:49 Then, sometime last year, I suddenly got a mail, and he had noticed my name in Scientific American.

00:02:56 He said, is this the same Koji Nakanishi who used to be in Alexandria?

00:03:00 Since then, we've started corresponding.

00:03:03 He happens to be a well-known Greek political cartoonist and critic living in Athens.

00:03:12 I'm going to visit him sometime next year. We're looking forward to this.

00:03:18 This will mean that I'll meet this guy in over 40 years.

00:03:23 That's what it is.

00:03:25 When you returned to Japan, it was almost like going into totally new culture.

00:03:31 Yes.

00:03:32 How has your schooling continued there?

00:03:34 All sorts of funny things happened.

00:03:36 I had to get a tutor and teach learning Japanese.

00:03:43 I could not write a thing.

00:03:45 My mother, I remember, she got the primary school text,

00:03:53 and she taught me how to write in Japanese on the boat way back to Japan.

00:03:59 I was more or less like a foreigner.

00:04:04 One small instance, which probably would be very funny for you people, is that I was on the beach.

00:04:12 This has nothing to do with chemistry, but I was wearing a crimson bathing suit.

00:04:19 I was laughed at by all the other people.

00:04:21 Look at that. He's wearing crimson.

00:04:24 You see, in Japan, it was pre-war.

00:04:26 Boys only wore black swimming suits, never crimson.

00:04:31 I see.

00:04:32 I was ridiculed. I remember that.

00:04:35 That was something you were not prepared for.

00:04:38 I had to get used to all sorts of things.

00:04:40 As a result, I still don't understand some subtle aspects of Japanese culture.

00:04:50 I also don't understand the subtle aspects of Western culture.

00:04:55 I'm one of those particular people who have no basis, neither West or East.

00:05:01 It's true.

00:05:02 You fit and you don't fit into the world.

00:05:07 Was there any particular time that you can point to and say,

00:05:14 my interest in science was piqued and after that I wanted to be a scientist?

00:05:22 Unfortunately, no.

00:05:24 Many people have nice stories about that, but in my case, no.

00:05:28 I simply became a scientist because there's no other place to get a job.

00:05:33 I see.

00:05:35 A very good practical reason.

00:05:38 In fact, I loved making models and ship models out of cardboard.

00:05:46 I wanted to become a shipbuilder, constructing and designing passenger ships.

00:05:53 But that was pre-war and didn't work out.

00:05:57 Somehow, I found myself becoming a chemist.

00:06:00 It really was.

00:06:01 It's chaotic because my high school college was just around the early 40s.

00:06:08 It was totally chaos.

00:06:10 You were still in high school when the war began?

00:06:13 The war started, I was still in high school.

00:06:16 Then when I entered college, the war was already on the way.

00:06:20 What do you remember from your high school years?

00:06:25 How did the war affect your education?

00:06:28 I must say that I was fond of chemistry in a sense.

00:06:31 My high school teacher, who unfortunately is dead now,

00:06:34 but he did have some influence on me.

00:06:37 So somewhere, although I didn't decide that I'm going to become a chemist,

00:06:43 I must have had something left over here that chemistry is not that unfavorable.

00:06:47 An image, you see.

00:06:49 So I was definitely going into some field of science.

00:06:53 That's for sure.

00:06:56 But because of the war, high school didn't affect it.

00:07:02 Then we went to Nagoya University, and then the war really became very bad.

00:07:09 Then we had to discontinue most of our classes and everything.

00:07:15 The chemistry department moved up into a deep mountain in Japan

00:07:21 to avoid the bombing and so on.

00:07:25 That is when I already entered the department of chemistry.

00:07:30 That's right.

00:07:33 My last two years in high school, a year and a half in high school,

00:07:40 there was also no formal training.

00:07:42 We were all sent to factories and being involved in steel works and things like that.

00:07:49 Then we all went to the university, and Japan was about to be defeated,

00:07:55 so we all went to the mountains.

00:07:57 So it was totally screwed up.

00:08:00 I think my chemistry knowledge was almost non-existent.

00:08:07 Somehow I survived.

00:08:10 I was exempted from military duty because I was in the science field.

00:08:16 It was a small private high school, the place I went to.

00:08:22 This was where?

00:08:23 In Konan High School, K-O-N-A-N.

00:08:27 It's rather small, but I'll tell you in a moment what happened to my classmates.

00:08:34 We were science and literature, and then the science class only had 35,

00:08:41 and the literature also, or art, 35.

00:08:45 So it's a very small one year.

00:08:47 I only had 70.

00:08:49 It's a small private, but fairly geared towards...

00:08:54 The university, essentially.

00:08:56 I mean, toward college preparation.

00:08:58 Yes, prep school type of thing.

00:09:02 Well, I missed most of the formal classes.

00:09:05 But amazingly enough, it's a small school of 35,

00:09:10 and of these, if you speak of how many went into academic teaching in chemistry,

00:09:15 we got five professors.

00:09:18 So I must say that my professor, the teacher at high school, must have had some influence.

00:09:24 Yes, and we still meet each other.

00:09:31 And then you went to the mountains.

00:09:36 Were you being given directions on how to make preparations?

00:09:40 You were working on explosives at that time?

00:09:42 Well, yes.

00:09:44 You see, instead of going to be drafted into the military,

00:09:49 we were sent to various naval or military research labs.

00:09:54 And my assignment was called to this, where they made the explosives.

00:10:01 It's a naval explosive institute, if you want to call it.

00:10:06 And this was in the mountains, you see.

00:10:09 And we were, being a chemistry major, we were all assigned to making some explosives.

00:10:15 But this was before, as I told you, my final years of high school was not proper.

00:10:23 Although we had already done some undergraduate organic labs.

00:10:29 And then university, almost hardly anything.

00:10:33 Then we went to this place and was assigned this organic reaction and making explosives.

00:10:40 It was not at that stage yet.

00:10:42 It was just simply making an epoxide and then opening that.

00:10:48 No, closing a halohydrin to an epoxide.

00:10:53 But having absolutely no experience in these kind of things,

00:10:58 I took a big flask about this size.

00:11:01 And then at the very center there was a small amount of solution.

00:11:06 And then from a dropping funnel, this big round bottom flask was already very warm, hot.

00:11:14 And then we had to drop this alkali.

00:11:17 And then instead of dropping it right onto this small amount of solution,

00:11:21 it went to the drop in the walls.

00:11:25 So the first drop, the whole thing cracked.

00:11:28 And that was a disaster.

00:11:30 And then I had to stop.

00:11:32 That was the last round bottom flask we had.

00:11:35 But I don't know whether that prejudices me or not,

00:11:39 but that was my first encounter with organic synthesis.

00:11:43 Ever since I've felt a big, tremendous inferiority complex towards organic synthesis.

00:11:50 I see.

00:11:51 But that gave me a good excuse because we were in the deep mountains.

00:11:56 And I had to go back to my home lab in Nagoya to fetch a new round bottom flask.

00:12:04 And that's where my fiancé was at that time.

00:12:08 So that gave me a good excuse.

00:12:11 Maybe it was not such an accident after all.

00:12:18 During the war, you had feelings of how things were going to end, how things were going to come out.

00:12:31 Well, no.

00:12:33 I was very simple-minded.

00:12:35 And I don't think I even thought about that too much.

00:12:39 And we were all brought up in the way that Japan has never lost a war.

00:12:44 And it was strictly this militaristic thoughts, you see.

00:12:48 And we were mostly trained that Americans are soon going to land on the mainland.

00:12:53 And then we, half seriously, we should sharpen our bamboos to be ready for the Americans, you see.

00:13:00 And then I, without being that serious, that's the only thing which went through my mind.

00:13:05 It's very anomalous if I think about it now.

00:13:10 But maybe because I was a very simplistic-minded person.

00:13:14 On the other hand, my wife, she's the same age as I am, but she always knew that Japan was going to lose.

00:13:22 And she didn't give a damn to what the military was saying.

00:13:26 So it's quite different.

00:13:27 And I think quite a few people thought like my wife did.

00:13:31 I wonder if it's a male-female kind of thing.

00:13:34 Yes, maybe she was more mature in thinking.

00:13:37 And, of course, she reads novels and things like that much more than I do.

00:13:41 So it's, yes, male-female plus...

00:13:48 Then after the war, you returned to Nagoya.

00:13:51 Yes.

00:13:52 And what were conditions like then?

00:13:54 Oh, it was complete...

00:13:58 Our university, fortunately the chemistry building was not bombed.

00:14:03 It was still standing.

00:14:06 But we had no reagents.

00:14:09 We had to really start from scratch, absolute scratch.

00:14:13 And the Americans, they all...

00:14:16 What did they call them?

00:14:18 The American army was in Nagoya, too, you see.

00:14:21 And surprisingly, the relation between the American army and the Japanese citizens

00:14:28 was very intimate, I must say.

00:14:31 And because I spoke English, I soon made some friends

00:14:37 with some American soldiers and army officers.

00:14:41 And I remember that there was the American Cultural Center in Nagoya.

00:14:48 This is when the MacArthur, the American army, or the American Cultural Center,

00:14:54 I don't know, the American government, I suppose,

00:14:56 set up these cultural centers in the major cities.

00:14:59 And that was the only place they had chemical abstracts.

00:15:03 And so I used to go there quite often on a bike

00:15:07 and then copy the chemical abstracts.

00:15:11 And that was in 1946, 47, 48, yes.

00:15:25 At the end of your undergraduate work, you just went directly into graduate work, I take it.

00:15:32 Well, yes, because at that time there was no industry yet, you see.

00:15:38 I mean, it has been devastated.

00:15:40 And so we just, and then it is the same today, too.

00:15:45 The government supported all the graduate students.

00:15:48 So we didn't have any other place to go.

00:15:50 So we just automatically, in my case, stayed for the graduate school.

00:15:55 And I went into, I joined a biochemical group.

00:16:01 The head was Professor Egami.

00:16:05 He's a well-known biochemist.

00:16:08 Unfortunately, he died.

00:16:12 And then Professor Egami, and then his assistant professor was Professor Hirata.

00:16:18 And he's probably, well, he's the center of natural products,

00:16:23 one of the big centers of natural products in Japan.

00:16:27 And quite a few famous people have come out of his school.

00:16:31 And so Egami and then Professor Hirata.

00:16:35 And I went more into, Hirata was, at that time, he was, I think he was already starting to have an interest.

00:16:44 This is in the late 40s, I think, starting to have an interest about all these bioluminescence and things like that, you see,

00:16:52 which is, I think, quite amazing.

00:16:54 Yes.

00:16:55 Yes, that a natural product chemist could start thinking even of what is the chemistry behind bioluminescence, you see.

00:17:03 Okay.

00:17:04 He was worried about the structure, but he was also worried about the chemistry behind it.

00:17:07 No structure, no, it was before those days, yes.

00:17:12 This was the days when people just took any plants, extracted something, do the structure determination, you see.

00:17:18 And it was when we didn't have any, for example, UV was unknown, okay, in the organic community.

00:17:29 In the States, yes, because you already had the Beckman DU instrument, which was sort of a, I think it's a quantum jump.

00:17:40 Plus, what is well known is, I think, in terms of structure determination on my field, Woodward came out with his two simple UV rules in 1941 and 42.

00:17:55 And this we did not know in Japan yet, okay.

00:18:00 And this is when he came out with the Woodward and then later the Woodward FISA, enone and diene rules.

00:18:06 Plus that and the Beckman DU, I think, made a big contribution to organic chemistry in the sense that they made the chemists realize

00:18:15 that spectroscopy is something that even organic chemists can use, you see.

00:18:20 But I did not know this until I went to Harvard in 1950.

00:18:27 I would rather say that, on the other hand, by fortune, probably because I went to the American Cultural Center and so on,

00:18:37 it was a time when paper chromatography had just become to be known.

00:18:47 Martin and Sinch later got the Nobel Prize, and that was in the late 40s.

00:18:52 And I picked it up, and then I was already doing that at Nagoya University, paper chromatography.

00:18:59 Okay.

00:19:00 Yes.

00:19:01 Okay, because I know you, well, we'll talk about Harvard in just a few minutes.

00:19:04 Yes.

00:19:05 Your first, so you essentially worked with Hirata.

00:19:11 Yes.

00:19:12 And your first work was on actinomycins.

00:19:14 Yes.

00:19:16 Can you tell me just a little bit about that?

00:19:18 Yes.

00:19:19 That is, actinomycin, as you know, is a peptide, and it's a very complicated structure.

00:19:26 And there was lots of interest in Japan already about antibiotics.

00:19:31 Hirata later, he made lots of contributions to antibiotics.

00:19:36 I must tell you that penicillin was also known in Japan during the war.

00:19:41 Oh, I see.

00:19:42 It turns out that, I found out later, that the British, well, and then the Americans,

00:19:47 they got together, and it was a super secret.

00:19:50 But during the war, there was an intimate collaboration between the U.S. and England, U.K.,

00:19:55 involving all aspects of chemistry, x-ray, spectroscopy, and so on, to get the structure and synthesis.

00:20:03 Now, in Japan, it is the late, I think, Professor Umezawa, who recently, unfortunately, died,

00:20:12 but it was called Green Stuff, and that was penicillin.

00:20:18 But people are still trying to purify it.

00:20:22 I think Hirata had a great interest already in those things,

00:20:25 and he was partly involved in this Green Stuff after the war.

00:20:30 I see. Okay.

00:20:31 And that turned out to be crude penicillin.

00:20:34 And as a result of that, he had some connections with pharmaceutical companies

00:20:42 who produced these antibiotics, and I think that's where actinomycin came.

00:20:48 And it's such brilliant red crystals, and we just simply did it in the very classical way,

00:20:56 only using paper chromatography as a modern tool, no UV, no infrared, of course,

00:21:02 and trying to first determine how many double bonds there were.

00:21:07 So I used to put it in the hydrogenator, yeah,

00:21:12 and you weighed it with a microbalance and tried to determine how many double bonds.

00:21:18 But, of course, depending on the catalyst, the purity, quality,

00:21:22 and with that quinonoid structure, you're never going to get a constant result.

00:21:29 So I spent, I think, several months until finally I think I got some results.

00:21:35 So at a progress report meeting, I proudly got up and said,

00:21:39 we determined the double bond numbers and so on.

00:21:42 But Professor Egami, the first word he mentioned is,

00:21:45 you're wasting your time.

00:21:47 If it fluctuates that much, what's the sense of doing it?

00:21:49 I still remember that.

00:21:53 Okay.

00:21:54 While you were in graduate school, before you finished,

00:21:57 you took an examination for the Garioa Fellowship.

00:22:05 Yes.

00:22:06 And what prompted you to do that?

00:22:09 Well, let's see now.

00:22:12 Japan at that time, they had a different system.

00:22:16 We simply go to graduate school and you get a Ph.D. or Doctor of Science

00:22:20 whenever the professor thought you had done enough.

00:22:23 And the minimum was ten years or so.

00:22:25 Oh, my.

00:22:26 Oh, yeah, minimum.

00:22:27 And then it was Roger Adams, I don't know what I told you,

00:22:30 but who came as a representative from the U.S.

00:22:34 to change the Japanese system into American system.

00:22:37 And he was the head of the so-called educational committee.

00:22:41 And Roger Adams was the one who changed,

00:22:44 responsible for changing the Japanese-American educational system

00:22:49 from primary school through the graduate school.

00:22:52 And so that's why we have the schooling system in Japan

00:22:56 is almost the same as in this country.

00:22:58 I see.

00:22:59 And that's when we have now the five-year for Ph.D. and so on.

00:23:02 Well, anyhow, I was under the old system.

00:23:06 And then I went, I like drinking even now,

00:23:13 but I went to a friend of mine living in the same apartment,

00:23:17 a drinking party, and he just said,

00:23:20 do you know that tomorrow it's called, well, American,

00:23:27 it's called the Gariowa system, which is the predecessor.

00:23:31 And one year before, from the following years,

00:23:36 it started being called the Fulbright Fellowship.

00:23:39 And there's going to be an exam held at the City Hall

00:23:43 for those who are interested in going to the States.

00:23:46 And why don't you go?

00:23:48 And so I had no idea about this.

00:23:50 I had not read about this.

00:23:52 But because I went for this drinking with my friend,

00:23:54 I decided I would give it a try.

00:23:57 So I went to the City Hall.

00:23:59 And because my English at that time was much better

00:24:02 than the average Japanese, I got the fellowship.

00:24:06 And as a result, I became quite, I mean, a celebrity.

00:24:11 My picture, it is myself and a few others, I think,

00:24:14 who passed the exam from Nagoya,

00:24:16 so our pictures are in the newspaper and so on.

00:24:20 And then, being a scientist,

00:24:23 I could choose wherever I wanted to go, you see.

00:24:26 And it's rather unusual,

00:24:30 but I finally decided.

00:24:34 I picked up one from the West, and that was Harvard,

00:24:37 and from the West, that is Caltech,

00:24:40 and George Beadle,

00:24:43 because at that time I was doing some chemistry

00:24:46 related to genetics.

00:24:48 And I was doing things which are very closely related

00:24:53 to what George Beadle was doing.

00:24:55 On the other hand, I had Harvard in mind also

00:24:58 because organic chemist.

00:25:00 And at that time, FISA's name was well known.

00:25:05 And we had just started hearing about the name

00:25:07 of this young genius called Robert Woodward.

00:25:14 And this is the time he was making some peptides.

00:25:18 And I decided to go to Harvard instead of Caltech

00:25:22 because if I go to Harvard, it's in Boston,

00:25:25 and then I can have a free trip across the country.

00:25:29 And then I can always visit Caltech on my way back

00:25:32 or on my way to.

00:25:34 And as a result, if I'd gone to Caltech,

00:25:36 probably I would nowadays be a molecular geneticist

00:25:40 or something.

00:25:41 But on the other hand, I went to Harvard,

00:25:42 so I'm an organic chemist now.

00:25:48 Tell me a little bit about your experiences at Harvard

00:25:51 working for FISA.

00:25:52 Yes, there's many things.

00:25:55 I was, anyhow, I think I was the first Japanese organic chemist

00:26:01 to spend an extended time at Harvard.

00:26:04 And FISA, well, first of all,

00:26:08 my organic chemistry was almost non-existent.

00:26:11 As an experimentalist, probably I was not doing too bad,

00:26:15 but my knowledge in organic chemistry.

00:26:18 And I go to Paul Bartlett's, I think it was undergraduate,

00:26:23 advanced organic.

00:26:25 And he started using these words,

00:26:28 SN1 and SN2, E1 and E2,

00:26:32 and I didn't have a clue what he was speaking about.

00:26:36 And then I found out that this was the so-called electronic theory,

00:26:39 and then so I had to start studying furiously,

00:26:45 reading books.

00:26:47 So this kind of thing was just not taught at all in Japan?

00:26:51 No, not at all.

00:26:52 We had never heard about those.

00:26:54 In fact, the electronic theory was hardly existing at that time.

00:26:59 So that's one thing.

00:27:01 Another thing is that's my first encounter with spectroscopy, too.

00:27:07 And before that, I might tell you one more thing.

00:27:11 FISA, I don't think he exactly knew how to handle me.

00:27:16 And eventually we became very close,

00:27:19 and I owed a tremendous amount to FISA.

00:27:23 And I remember the first I called,

00:27:29 I went to Harvard on a Saturday or Sunday,

00:27:31 went up to his office,

00:27:33 and he was there, typical FISA, with a dirty lab coat and so on,

00:27:38 doing experiments.

00:27:39 Yes, and the towel hanging out.

00:27:40 Yeah, towel, that's right.

00:27:42 And he gave me a project.

00:27:44 It was a synthesis of naphthaquinone,

00:27:47 which is related to anti-malaria things.

00:27:50 He just gave me the project and sketched out the reaction,

00:27:53 do this, and that's it.

00:27:55 Okay?

00:27:56 And then I started working on this furiously.

00:28:01 And it was a so-called, you make a naphthaquinone,

00:28:05 and then with an alkyl chain,

00:28:09 and there's a so-called Foucault oxidation,

00:28:11 which chops down the alkyl little by little.

00:28:16 Okay?

00:28:17 And I don't know whether you know,

00:28:18 but FISA wrote after Foucault had died,

00:28:22 he wrote, I think he compiled all his papers

00:28:25 and wrote it for Foucault.

00:28:27 He assigned this to me.

00:28:29 And he didn't bother me for two, three months.

00:28:34 Then he came back from a trip,

00:28:36 and by this time I had done,

00:28:38 because I knew about paper chromatography, you see.

00:28:41 And when you're comparing a series of naphthaquinones

00:28:44 with different side chains,

00:28:46 paper chromatography is ideal.

00:28:48 And I did this time-wise in different time aliquots.

00:28:53 And I got a beautiful set of spots, you see.

00:28:56 And I think FISA had not known about paper chromatography yet.

00:29:00 At least it was not used in his lab.

00:29:03 So when he came back, he was astounded.

00:29:06 And then he became, well, fortunate.

00:29:09 So that made a whole difference in your relationship.

00:29:11 Yes, very fond of me.

00:29:13 And then he was very kind to me.

00:29:16 And it was only he supported me for the second year.

00:29:21 So, and then I don't know whether I told you about the stuffed bat.

00:29:28 Should I tell you?

00:29:29 Yes, I think that's a wonderful story.

00:29:31 I think that should be told.

00:29:33 It's written in one of his essays.

00:29:35 But on the second year, he just,

00:29:41 there was always a stuffed bat in his office, in his lab.

00:29:46 And he just said, you know what this is?

00:29:48 Of course I didn't know what it was.

00:29:52 As you know, FISA is a very, he's a nationalist.

00:29:55 And, well, he's dead now, so I can say this.

00:29:59 But as is well known, he's also invented the napalm bomb.

00:30:04 And his idea was to use this bat.

00:30:08 And when they are carried way up,

00:30:11 because of the low pressure and low temperature,

00:30:14 they start sort of hibernating and they freeze, the movements.

00:30:19 And when they are brought down again to normal atmosphere,

00:30:22 normal temperature, they start beating their wings.

00:30:26 So his idea was to connect under the wings a time bomb.

00:30:32 And then take them on a military plane,

00:30:37 and then go over Tokyo.

00:30:39 And then in a big basket bomb, drop them over Tokyo.

00:30:43 And then the basket would open.

00:30:45 And then all the bats would, by then,

00:30:48 the frozen bats would come alive again,

00:30:51 start beating their wings.

00:30:53 And then that will set the time bomb.

00:30:56 And the bat would go under the roofs of various houses

00:31:01 and the Tokyo houses was mostly wood those days.

00:31:05 They would start fire all over the place, you see.

00:31:08 And I think he was supported by the military.

00:31:12 And his final test was done somewhere in New Mexico.

00:31:18 And fortunately or unfortunately, it was near a hangar

00:31:22 where it had lots of military planes.

00:31:25 So it succeeded in a sense,

00:31:27 but all the bats flew into the hangar

00:31:29 and blew up the whole thing.

00:31:31 And as a result, immediately it was banned.

00:31:35 And the military stopped its funding and everything.

00:31:38 And he kept this as a memento.

00:31:45 You mentioned it before.

00:31:47 About the spectroscopy.

00:31:49 Yes, that's when your love affair with spectroscopy began.

00:31:52 I had not even heard about infrared spectroscopy at the time.

00:31:56 This was in 1951, I think.

00:31:59 My lab mate was Costa Agnostopoulos.

00:32:04 He's a huge guy.

00:32:06 He's doing very well at Monsanto now.

00:32:09 High executive.

00:32:12 And when I first carried out my first reaction,

00:32:20 which had a carbonyl group,

00:32:24 that was the very first reaction.

00:32:26 I filled the crafts and made a carbonyl onto naphthalene,

00:32:31 substituted naphthalene.

00:32:33 And I tried to...

00:32:35 Well, if that had gone well, I should have had a keto group.

00:32:38 And as you know, in those days,

00:32:40 you had to make a derivative of a carbonyl.

00:32:43 First recrystallize, get the elementary analysis,

00:32:46 and then you do a reaction,

00:32:48 and then you have to make a derivative of the keto group,

00:32:51 and then another analysis, and so on.

00:32:53 But he said, well, just come with me.

00:32:57 And then he took me to the room

00:32:59 underground of the basement of Converse.

00:33:02 And that's very fortunate.

00:33:04 They had the second commercial automatic recording infrared

00:33:09 made by the Baird Company.

00:33:12 And I remember clearly that he did something.

00:33:15 He put it in a cell, which means I understand now.

00:33:18 And he said, watch this, and there's a roll of paper,

00:33:21 and then the needle starts moving like this.

00:33:23 And all of a sudden, at about 5.8 microns, so-called now,

00:33:27 it all of a sudden starts moving way down,

00:33:30 and sharp, it goes up again, you see.

00:33:32 And he told me, you've got the keto group.

00:33:36 And, well, I was dumbfounded.

00:33:40 I didn't know what the hell was happening.

00:33:42 Well, that turned out to be my first encounter with infrared.

00:33:46 I still have this chart with me.

00:33:49 And somehow, I got very interested in spectroscopy at that time.

00:33:54 And the infrared was still new, even at Harvard, for many people.

00:34:00 And I think Woodward was, again, one of the pioneers to use this.

00:34:04 But anyhow, I started within the FISA group.

00:34:07 I went to FISA.

00:34:08 Within the FISA group, a small group, about six or seven of us,

00:34:13 and we met every week and had a small gathering,

00:34:19 introducing new papers in spectroscopy, including UV and infrared.

00:34:27 And then I came back to Japan in 1952,

00:34:31 and I had some lecture notes and so on.

00:34:33 I got these together with my notes and started a series.

00:34:39 I first wrote one review article, like an article review style,

00:34:46 in a Japanese monthly popular chemical journal.

00:34:51 And this had, I must say, quite an influence.

00:34:55 I mean, tremendous response.

00:34:58 And the publishers liked this.

00:35:00 So starting next year, I started a series,

00:35:03 the so-called, what you call now, based on groups, the group frequencies.

00:35:08 Alkanes, alkenes, aromatics, carbonyls, and so on.

00:35:12 It continued for one year.

00:35:14 And after the end of the year, I compiled it into a book.

00:35:18 And once you start writing this, your name becomes famous

00:35:21 and you're asked to give a lecture here and there.

00:35:24 So I was forced to learn infrared.

00:35:28 And somehow I became a so-called, quote-unquote,

00:35:31 a qualitative infrared expert.

00:35:35 Then that is in Japanese.

00:35:38 So this is now published around 1953 or thereabouts?

00:35:42 Yeah, no.

00:35:44 No, it is a little later than that.

00:35:47 Yeah, maybe 54.

00:35:50 I don't remember.

00:35:51 Maybe 57, 58.

00:35:54 Oh, yes, I know what happened.

00:35:56 Before that, I returned to Japan when I was 52.

00:36:01 And then I'll come back to the infrared in a moment.

00:36:05 But then I had a very, I still have it now, what you call now, a TB.

00:36:13 But it's not serious at all.

00:36:15 So I was asked by the doctor not to go to the lab too much.

00:36:19 So I stayed at home.

00:36:21 And I recovered in about 10 months.

00:36:25 But during that time, I translated Fieser's Organic Chemistry.

00:36:30 And that was a big one.

00:36:32 Three volumes, it came out in Japan.

00:36:35 And that helped me tremendously financially

00:36:39 because the salaries of university people at that time was minimum.

00:36:44 You could just barely survive.

00:36:46 And I had this extra income from the Fieser's book, which is very popular.

00:36:51 And then after that, I wrote this infrared book.

00:36:54 Was this the text or the Fieser book?

00:36:56 No, it was his book, the Organic Chemistry.

00:37:00 Okay.

00:37:01 On the other hand, his textbook of Organic Chemistry, the very famous one,

00:37:06 and I managed to have it reproduced in English in Japan by a Japanese publisher.

00:37:14 And this was the first so-called English written book post-war,

00:37:20 which was published in Japan.

00:37:22 And this was very popular.

00:37:25 I see.

00:37:26 And I think it has had a tremendous influence on the Japanese,

00:37:29 at least in Organic Chemistry.

00:37:31 Lots of schools use this textbook of Organic Chemistry.

00:37:35 Yes.

00:37:36 Yeah.

00:37:38 Now, you were married in 1947,

00:37:42 and your wife did not come to the United States with you.

00:37:48 Well, I went to the States in 1950, and we had a daughter in 1950.

00:37:54 And, of course, the Fulbright or whatever, Gary White was called,

00:37:58 only paid for my fare.

00:38:01 So it was almost unthinkable to go with your wife and family.

00:38:07 Just to describe what sort of a place Japan was,

00:38:12 we were brought to the States in a military plane,

00:38:18 and we were served what you now call Kentucky Fried Chickens.

00:38:23 I was so excited just to see the chicken.

00:38:26 I haven't had that for years, you see.

00:38:28 I still remember that, just having a chicken leg

00:38:30 served on a military plane coming to the States.

00:38:33 I see.

00:38:34 That was a pretty grim life at that particular point for you.

00:38:38 Oh, yeah, yeah, yeah.

00:38:41 Now, after you came back to Japan,

00:38:44 did you have to do any further work toward your Ph.D.?

00:38:47 Yeah, yeah.

00:38:49 I was still under the old system, so I did some further work.

00:38:53 I got my Ph.D., I forgot, in 1950.

00:38:56 When was it?

00:38:57 1954?

00:38:58 1954, yeah, 1954.

00:39:00 That's right.

00:39:01 Okay.

00:39:02 1954.

00:39:03 That's right.

00:39:04 And then you stayed on it, Nagoya?

00:39:06 Yes, for four or five years.

00:39:08 Okay, with?

00:39:09 Hirata.

00:39:10 I became the associate professor or assistant professor,

00:39:13 and Hirata, by that time, had split from Egami,

00:39:16 and he had become the organic professor,

00:39:19 and I became his assistant professor.

00:39:22 And when I became the assistant professor,

00:39:25 he went to Harvard to work with FISA for one year.

00:39:28 I see, I see.

00:39:31 Then I stayed there as a lecturer assistant professor,

00:39:37 and then I went to this Tokyo Kyoiku University,

00:39:42 which is nonexistent now.

00:39:44 Now it's called the Tsukuba University,

00:39:46 which is doing fairly nicely now.

00:39:49 And I went there, I forgot, that was in 19...

00:39:53 When was it now?

00:39:55 I think it was something around 59 or 60, thereabouts.

00:40:00 Yeah, yeah.

00:40:01 Okay.

00:40:02 1959.

00:40:03 Yes, 1959.

00:40:06 I know that was a federal university.

00:40:11 For that time, it was quite unusual.

00:40:13 I remember I was the youngest in the whole of Japan.

00:40:16 You were the youngest full professor of organic chemistry

00:40:19 in all of Japan at that particular point.

00:40:21 I was very lucky, I must say, because no one ahead was...

00:40:24 Yeah.

00:40:25 There was no one ahead.

00:40:26 Okay.

00:40:27 That primarily came as a result of your work in IR,

00:40:30 and your being well-known.

00:40:32 Yes, because I had an interest in spectroscopy,

00:40:35 I already had interest in physical constants,

00:40:39 and I think I was fairly famous.

00:40:42 Yeah.

00:40:43 You've done a lot of publishing in the natural products field as well.

00:40:47 Yes, around that time.

00:40:48 Okay.

00:40:49 I just finished my infrared book thing,

00:40:52 and I had compiled this infrared, which I wrote in Japanese,

00:40:56 and then I remember in 1960, there was the first...

00:41:01 I returned to Japan in 1950.

00:41:03 For ten years, I was in Japan,

00:41:05 during which time I'd moved to Tokyo, Kyoiku University,

00:41:08 where I was, and then in 1960,

00:41:10 there was the first IUPAC, Natural Products Symposium,

00:41:15 and the Japan people were already planning to have.

00:41:19 This was an IUPAC,

00:41:21 and it was supposed to be held every two years, you see,

00:41:25 and my senior professors, because I spoke English,

00:41:30 and I'd just come back from the States

00:41:33 and fairly used to the so-called Western chemistry,

00:41:37 I had been sent to Australia

00:41:42 to see how the whole thing was organized and so on.

00:41:47 They were planning to have the next IUPAC?

00:41:50 It turns out that, yes, the next one's already decided

00:41:54 it's going to be held in Prague.

00:41:56 That was in 1962.

00:41:58 And then 1964, it was, I think,

00:42:00 they were thinking of approaching the IUPAC to have it in Japan.

00:42:03 I see.

00:42:04 So they sent me to Australia to see.

00:42:06 Right.

00:42:07 Yeah.

00:42:08 And I had this infrared book with me in Japan, in Japanese,

00:42:13 and at the Australian hotel, breakfast,

00:42:19 unfortunately or fortunately,

00:42:21 I happened to be caught between Carl Gerasi and Derek Barton.

00:42:25 Barton, Gerasi, and Woodward

00:42:27 were the three giant names at that time,

00:42:29 and I was just a Japanese timid,

00:42:31 first time out of Japan, you see, in 1960.

00:42:34 And so I showed them this infrared book,

00:42:37 very timidly, on the breakfast table,

00:42:39 and they both looked at it,

00:42:41 and I think both of them said,

00:42:43 why don't you try to do this in English?

00:42:46 Because it was, as far as style goes,

00:42:50 I think it was the first so-called picture book, you see,

00:42:53 and very easy to pick up data and so on.

00:42:57 So I went back to Japan,

00:42:59 and I found a friend of mine who was very good in stenography.

00:43:05 She was Japanese.

00:43:07 And from morning to night,

00:43:10 I finished the whole thing, the translation,

00:43:14 just dictating it to her in about 7 or 8 days.

00:43:18 And then she came up with the typing,

00:43:21 and a friend of mine did the design of the cover, an artist,

00:43:25 and then, very fortunately,

00:43:28 I think it was accepted very well in the States and other places,

00:43:34 and I became rather well known as a qualitative infrared man.

00:43:44 When were you first introduced to NMR?

00:43:48 Oh, that was much later.

00:43:50 Again, in Tokyo, this was...

00:43:54 I should have had my...

00:43:56 When did I... It was in...

00:43:58 Okay. It was in late 50s.

00:44:01 Okay, fine.

00:44:03 I think so. I think that's what it was.

00:44:06 That's right. Late 60s. Late 50s.

00:44:10 And, yes.

00:44:13 And did you already see possibilities there for utilizing...

00:44:18 Oh, yeah. Yeah.

00:44:20 I think by 1960, at least on your bibliography,

00:44:23 you were publishing papers on the NMR spectra

00:44:26 of metabolites of Manuscuso and...

00:44:30 Oh, yeah. Yeah, yeah.

00:44:32 Yes, that's right.

00:44:34 That reminds me.

00:44:36 I was working...

00:44:38 This was when the... I still have this one.

00:44:41 For me, it's a very historical NMR.

00:44:43 I was working on a triterpene called pristimerine.

00:44:47 Okay, and it is a...

00:44:49 It's an Indian drug which is...

00:44:52 It's a red pigment, and when I left Harvard,

00:44:55 it was sent to FISA from...

00:44:57 He has many Indian students,

00:44:59 and Bhatnagar was the name of the Indian chemist,

00:45:03 or he was a colonel.

00:45:05 He sent it to FISA for structure,

00:45:07 and he gave that to me, and I couldn't finish it.

00:45:11 So I asked FISA,

00:45:13 could I bring it back to Nagoya and continue, he said.

00:45:16 And so he gave me that project, you see, pristimerine.

00:45:20 And then it turns out, Alan Johnson,

00:45:23 who was at Nottingham and later Sussex,

00:45:26 and he unfortunately died 3 years ago, rather young,

00:45:31 and it was a very complicated structure,

00:45:34 and he later told me he used to call it the PhD compound

00:45:40 because so many PhDs have been made on the structure.

00:45:46 And then it turned out to be the same compound,

00:45:50 but I measured the NMR,

00:45:52 and this was still on those very narrow strip charts,

00:45:57 and we could just barely count the methyl singlets,

00:46:01 and I think I counted...

00:46:03 I may be wrong, but 7 methyl singlets, you see.

00:46:07 Alan Johnson had not measured NMR yet,

00:46:09 and from that I could come out with the structure.

00:46:12 I see.

00:46:13 So that was, for me, it was very memorable,

00:46:16 and that was my first time I used NMR.

00:46:19 And for a change, the structure of pristimerine was correct, I think.

00:46:24 I see.

00:46:26 Yeah.

00:46:28 And that, I think, I got interested in NMR, of course, since then.

00:46:34 Yes.

00:46:35 And then the monoscrubline was a little bit more detailed,

00:46:39 with decoupling and coupling constants and so on.

00:46:42 Yes, that was more proper.

00:46:43 I see.

00:46:44 I see.

00:46:45 Okay.

00:46:46 At this point, the end of the 50s, the early 60s,

00:46:52 before you went to Hoku,

00:46:55 what was determining your choice of problems?

00:47:01 That is, you worked on a lot.

00:47:03 Most of your publications were structure determination

00:47:05 and usually bioactive compounds.

00:47:08 Yeah, yeah.

00:47:09 I think that's what it was, still the same.

00:47:12 But my tendency, my emphasis was more on usage of physical constants,

00:47:19 which still is the same.

00:47:22 And rather than, of course, X-ray was not that popular at that time yet,

00:47:28 but I had a tendency of not doing too many chemical, well, chemical, yes,

00:47:33 but I would rather put it this way.

00:47:35 I tried to use the physical constants maximally, you see.

00:47:40 And I remember…

00:47:41 Physical constants meaning the spectroscopy.

00:47:44 Spectroscopy.

00:47:45 Yes, yes.

00:47:47 And I remember giving a talk at the Japanese chemical annual meeting,

00:47:57 the structure of whatever it was deduced from physical constants.

00:48:02 And physical constants was, I think,

00:48:06 I may have been the first person to use that name in Japan,

00:48:10 in the organic community.

00:48:12 And I know lots of elderly people did not like that title at all.

00:48:18 You should do more proper chemistry.

00:48:23 There's always a tendency to watch out for the young.

00:48:27 But still, that's still, I think it's still in my tendency

00:48:35 of doing structure terminations.

00:48:37 I tend to put more emphasis on methodology rather than the structure.

00:48:45 Yes.

00:48:46 Yes.

00:48:47 And because structure is something, well, it's simply if it's done,

00:48:52 a new structure, there's so many numerous new structures now,

00:48:55 it's just another structure to remember, you see.

00:48:57 Right.

00:48:58 But if you come up with some new methodology,

00:49:02 it has more general applications which other people can use.

00:49:05 And it has a sense of longer-lasting impact on…

00:49:09 Yes.

00:49:10 And so I feel a challenge, especially in using various spectroscopy

00:49:16 in a combined way and trying to use like infrared, NMR, UV, PK, CD,

00:49:23 all of these, use it maximally.

00:49:25 Yes.

00:49:26 Yes.

00:49:27 Yes.

00:49:28 Yes.

00:49:29 Yes.

00:49:30 Yes.

00:49:31 In 1963, you…

00:49:49 Can use a little rest too.

00:49:52 We were all taught to just kamikaze.

00:49:55 I see.

00:49:56 Yes.

00:49:57 That's where the word kamikaze comes from, suicide, sort of.

00:50:00 Yes.

00:50:01 Bamboo is like a suicide.

00:50:03 Oh, of course.

00:50:04 That's right.

00:50:05 I mean, yes, the sharpening of the bamboo against people with guns and bombs.

00:50:08 It's a suicide.

00:50:09 Uh-huh.

00:50:10 Uh-huh.

00:50:11 Oh, I thought that you were going to fight with the bamboo.

00:50:14 Oh, yeah, fight.

00:50:15 Oh, you would fight, but it would still be suicidal.

00:50:17 Fight, but it's almost like a suicidal.

00:50:19 Yes, of course.

00:50:20 Of course.

00:50:21 Not yourself.

00:50:22 Yes, right.

00:50:23 And you know the Americans, they're over there with the guns and whatnot and bombs,

00:50:27 and we're just going there.

00:50:29 Right.

00:50:30 Yeah.

00:50:31 Yeah.

00:50:32 Yeah.

00:50:33 But that was very striking to me.

00:50:38 And then there was another thing, which is just as well one of the other pictures of

00:50:46 post-war Japan you gave was picking in the fields after they'd already harvested.

00:50:50 Oh, yeah.

00:50:51 I mentioned.

00:50:52 I was going to.

00:50:53 But that was very striking.

00:50:54 I thought this was going into too much detail.

00:50:55 I see.

00:50:56 It was very striking to me.

00:50:57 Oh, I could have gone on and on about post-war Japan.

00:51:00 I'm sure.

00:51:01 And how the FISA money helped me.

00:51:03 I was the first one in my lab to own a scooter.

00:51:06 I was so proud of it, and that was the FISA royalties gave me.

00:51:10 Oh, yeah.

00:51:11 The book, translation of the book.

00:51:13 You know, I had a friend when I was in graduate school, a fellow next to me by the name of

00:51:18 Hiroshi Minato.

00:51:20 Oh, yes.

00:51:21 Did you know Hiroshi?

00:51:22 Oh, of course.

00:51:23 He also translated some of FISA's work.

00:51:26 He died tragically.

00:51:27 Yeah.

00:51:28 Falling from a ladder.

00:51:29 Yes.

00:51:30 Oh, I knew him very well.

00:51:31 Oh, I wondered if I'd asked you about that last time.

00:51:33 I guess I didn't.

00:51:34 Oh, he's a Paul Bartlett student.

00:51:36 Yes.

00:51:37 Yes.

00:51:38 We were on the same bench, essentially.

00:51:39 Yeah, if you know him.

00:51:40 Yeah.

00:51:41 Do you know Sakurai?

00:51:42 Yes.

00:51:43 He was also there at the time.

00:51:44 Yes.

00:51:45 He succeeded me at Sendai.

00:51:46 Oh.

00:51:47 Oh, and he's done extremely well.

00:51:48 Yeah.

00:51:49 And he's the, okay, when I left, he succeeded my lab and converted that into Silicon Lab.

00:51:55 Okay?

00:51:56 Okay.

00:51:57 And one of the Ginkgolite group members is his associate professor now.

00:52:01 I see.

00:52:02 Nakadaira is his name.

00:52:03 Yeah.

00:52:04 Yeah.

00:52:05 What was the older fellow who was there?

00:52:09 Was a much older fellow who had come as a post-doc one year.

00:52:14 Funahashi?

00:52:15 Yes, Funahashi.

00:52:16 Just about the same time that Sakurai was there.

00:52:19 But Sakurai was a young man at that time.

00:52:21 Yeah, Funahashi.

00:52:22 I see.

00:52:23 Funahashi, Funahashi.

00:52:24 I remember him so well.

00:52:25 Oh.

00:52:26 From Osaka University?

00:52:27 Oh, you wouldn't remember, right?

00:52:28 May have been.

00:52:29 But he was, he's older than I am.

00:52:32 Oh, yes.

00:52:33 What?

00:52:34 Oh, yes.

00:52:35 In the early 60s, he must have been 45, 50 years old.

00:52:41 Okay.

00:52:42 Okay.

00:52:43 Well, maybe, yeah.

00:52:44 Okay.

00:52:45 So he would be much older than you.

00:52:46 Oh, yeah.

00:52:47 Yeah.

00:52:48 Okay.

00:52:49 Then it's the same Funahashi.

00:52:50 Yes.

00:52:51 I see.

00:52:52 I see.

00:52:53 Sorry, we have to get again together, but we'll do it sometime.

00:53:09 Okay.

00:53:10 Yeah.

00:53:11 Funahashi.