B.R.S.M. The road to Tet. Lett. Is paved with good intentions


Holiday Reading 1: Perspectives and Humble Beginnings

Thanks to DrFreddy and Young Padawan for providing the inspiration for this post! Happy New Year!

I have always enjoyed learning about the history of reactions and strategies; for me the who and when are often as interesting as the what as they put the chemistry in context, and often make things a bit easier to remember because they help with the big picture. Plus, we all like to have stories about famous chemists to tell when we get together over coffee (or beer).

Late last year an interesting discussion took place over at Synthetic Remarks, sparked by the autobiographical piece published by Stork in the Tetrahedron issue celebrating his 90th birthday.[1] The article itself is well worth a read for some interesting anecdotes interspersed with a little chemistry. I particulary enjoyed Stork's offhand description of his marriage:

"My progress in the lab was only moderately affected by getting married to Winifred Stewart, the same young woman that I had met at St. Petersburgh Junior College some years before. As I recall, I asked one of my lab partners to watch over a reaction while I went to meet my future wife in the office of the justice of the peace who was to marry us"

Well, I guess you don't get that good by wasting time on your personal life! I also liked the story of his and Woodward's recruitment as promoters for the journal Tetrahedron at its launch:

"...one event I remember was the launching of Tetrahedron. Captain Maxwell, as the editor of the journal in question was known, had invited in April 1957, a number of guests in a townhouse in downtown New York to mark that event. During the celebrations, Maxwell placed a bet with some of the guests, namely Bob Woodward, Bill Doering, Carl Djerassi, and myself that the circulation of Tetrahedron ‘will not exceed 2499 copies’ by April 24, 1961. The bet, which was witnessed by Sir Robert Robinson, was for 100 gold guineas. This was a clever bet, because Maxwell would essentially get four salesmen for his new journal in exchange for a relatively small amount of money. Time passed, and one day I received a phone call from Woodward who said ‘you know, we won the bet’. I did not know, but I eventually got a call from Maxwell who suggested I meet him in a townhouse downtown where, after some champagne, he gave me a copy of a letter from a bank in Basel stating that 100 gold sovereigns (the bet had been changed to sovereigns by mutual agreement) was waiting for me in the branch of the Swiss bank in New York. I went there, carrying a French newspaper that I thought would give me some appearance of respectability, and was introduced to a vice president who did, in fact, hand me a small bag containing 100 gold sovereigns. This, after many years, is worth quite a bit. In 2011, at the time of this writing, 100 gold sovereigns equal in excess of $30,000!"

There are also a number of the infamous 'car stories' for which Stork is quite well known.[2]

Following DrFreddy's post, commenter Young Padawan asked if anyone knew of  any other such pieces on the lives of famous chemists and a list was created:

Steve Ley:

Tetrahedron, 2010, 66, 6270-6292. (DOI: 10.1016/j.tet.2010.05.049)

Larry Overman:

Tetrahedron, 2009, 65, 6432-6446. (DOI: 10.1016/j.tet.2009.05.067)

Robert Grubbs:

Tetrahedron, 2004, 60, 7117-7140. (DOI: 10.1016/j.tet.2004.05.124)

K. C. Nicolaou:

Tetrahedron, 2003, 59, 6683-6738. (DOI: 10.1016/S0040-4020(03)00943-8)

David Evans:

Tetrahedron, 1999, 55, 8589-8608. (DOI: 10.1016/S0040-4020(99)00436-6)

There are some great stories contained within these pieces. They're surprisingly easy to read and well worth a look! Particularly entertaining is Nicolaou's for its 21mb of Greek pottery and mind-boggling schemes, as well as tales of his first forays into 'synthesis':

“My Uncle John provided me not only with a warm place to stay, but also with my first ‘laboratory’ where I could practice making cakes in his confectionary shop. There I quickly learned the art of making pastry, and I developed a love for it and a taste for the ‘synthesized’ products. In fact, I was flattered by several local professionals who thought that I was so creative at making pastries and birthday cakes that upon completion of high school I should stay in Cyprus where “I had a great future ahead of me practicing the art””.

Since the earlier discussion in the comments I managed to find the story of Padwa's imprisonment in the Buffalo chemistry department mentioned by Young Padawan:

"It was in late January 1977 that a winter storm dropped more than four feet of snow in Buffalo over an 8-h period.By the early afternoon I was stranded in my office since a state of emergency was in effect, with all nonessential vehicles barred from the streets. Because the roads were impassable,I was unable to return to my home for 3 days. About 30 disoriented students and a few faculty managed to survive on food procured from the vending machines in the building, and we slept on the floor of our laboratories and offices. Not a particularly pleasant memory, but one that was certainly unforgettable"

Albert Padwa in J. Org. Chem., 2009, 74, 6425 (DOI: 10.1021/jo901300x).[3]

Does anyone know of other good stories in the literature?


1. Okay, so the post was actually about the rather amusing graphical abstract of said piece:

2. A current academic who postdocked for Stork told me that while he was at Columbia Stork was involved in a car crash (allegedly his own fault for running a red light). Chinese whispers eventually culminated in someone coming into the lab and informing the group that Stork had died in hospital, when in fact he'd only suffered minor injuries and was released later that day. Apparently the reaction when he entered the lab that evening was something to behold.

3. I did try and post this in a comment a couple of times but it never showed up. Guess it got marked as spam.

Comments (10) Trackbacks (0)
  1. Not really a paper, but there was a book series called “Profiles, pathways and dreams” that contained autobiographies of many top dogs like Dewar or Nakanishi. I highly recommend to find and read Dewar’s “Semiempirical Life”.

  2. Oh I really enjoyed that 🙂

  3. I’ve been meaning to read more of those – the only one I’ve read so far is Prelog’s “132 Semesters of Studies of Chemistry”, which was very enjoyable. Benfey and Morris’s book on RBW also has some great stories and photos. I got my copy cheap on eBay; it’s marked ‘Property of Imperial College Library’, hopefully it’s actually withdrawn and not stolen!

  4. @BRSM – Great post. I second @Alex’s comment about PP&D, a great series….my favorite is Bill Johnson, who relates a story about a mentally unstable grad student bringing a gun to lab…

    Also of note, an old story about Stork I’ve heard. At a conference in Miami, Woodward began with “This material I’m about to relate has never before been heard in the Western hemisphere” Stork, immediately following, led off with “The work I’m about to disclose has never before been heard in Miami”

  5. I am reading “The Way of Synthesis” by Hudlicky and Reed. Like you, I think half the fun comes from the history/ personal stories from the lab. This book is full of them. Highly recommended.

    • I do own (and have read) that book, and I think the personal recollections are an excellent idea. I particularly enjoy the ones for the Taxol and vernolepin sections, I guess because they were both the biggest targets of their days and it’s very interesting to hear from the people who were there. I also love the Taxol Time song (to the tune of Tulsa Time), apparently once performed at a Gordon Conference. I do find that the constant putting down of today’s chemists, journal editorial practices, reported yields etc. does occasionally grate, especially on rereading, but the comments are often fair. On balance, a great book for the chemist who wants to learn more classic syntheses and synthetic history and doesn’t mind reading quite an opinionated work.

  6. Wow..i didn’t want to say, but your right about opinionated. Seems the one author may have some grudges out there (which is natural in our field, I suppose…)

    Anyway I am going through piecemeal since its as thick as the bible. I wonder how long it took you to read!


  7. P.S. That vernolepin synthesis. That is especially interesting to me coming from Pitt when that went down years ago. There is at least one professor I know who was around at that time and has some good stories to tell about Danishefsky’s and Grieco’s rivalry…..or rather how it turned into a rivalry….great stuff.

  8. Another great paper full of anecdotes is the Nicolaou/Baran review on the TS of the CP molecules (ACIE 2002, 41, 2678) – scaring that Baran gave his compounds names like “christmas compound” or “New Years Eve compound” hmm?

    And I wonder if sleeping beside an NMR secures a good recreation, but maybe it boosts creativity 😉

  9. The Tetrahedron Prize essays are great. Also, I always enjoyed reading the obituaries at the beginning of the bound individual volumes of Organic Syntheses. It gave a lot of perspective as to where each chemist came from and brought them more to life as human beings.

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