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Gilbert Stork, 1921-2017

Word reached me late yesterday that Gilbert Stork had died. His most recent paper was published just last month in Org. Lett., and included what will surely become a famous footnote in the chemical literature.

22. A plan for conversion of 33a to 1 was (with various deprotections/protections) C4-CH2OH to C4-CO2H, followed by Barton’s conditions to change C4-CO2H to C4-OH. . .At this point, we realized that we did not have enough material (a few milligrams) to go through the several steps for this conversion. One would have to restart the whole synthesis. But I (G.S.) am now 95 years old…

Prof. Stork was one of the great organic synthetic chemists. He was born in Belgium and came to the US in 1939 when his family emigrated in the nick of time, and got his PhD at Wisconsin in 1945. He took a position at Harvard the next year, and moved to Columbia in 1953, where he stayed for the rest of his career (which is equal to the rest of his life – Stork became an emeritus professor, but as that above example shows, he never truly “retired”). Here’s an overview (PDF) of his career in organic chemistry from the Baran group at Scripps, and even if you’re not in the field, you can imagine that in over fifty solid years of high-level work you can cover an awful lot of ground. He was one of the last links, perhaps the last, to the heroic age of organic synthesis. All those famous names from the mid-20th century? He knew them; he was one of them.

Stork did total synthesis of natural products, taking on very hard problems and solving them elegantly. I think it’s fair to say that R. B. Woodward’s achievements and reputation always cast some shade in his direction, but there are very few others in his league. Prof. Stork also made a number of contributions to mechanistic understanding of reactions, and added no small number of transformations of his own to the list. Enamines, silyl protecting groups, radical cyclizations, stereospecific synthesis in general – his fingerprints are all over these and more, all of them fundamental classes of compounds and operations in organic synthesis.

And he was always a gentleman – this article will get across some of his personality. Stork’s wit was well known, but you never hear stories of it being used maliciously (and if you haven’t heard that of other famous chemists, you should be more familiar with the history of the field!)One of the words that comes to mind when discussing him and his work is “grounded”. Stork had a very clear idea of what chemistry was good for and what it could contribute, but at the same time he knew that it was not the only worthwhile thing in the world. Here’s a quote from him on organic chemistry in general:

“The toughest question to ask in synthetic organic chemistry after the work is done is: what have you learned? And you can have extraordinarily complex things. They look complex as hell. Maybe they have 80 asymmetric centers and maybe the answer is, [you’ve learned] nothing. I mean, you could have learned that humans are capable of enormous focused efforts and are capable of sticking with a problem which is extraordinarily complicated. On the other hand, if somebody makes polyethylene, as somebody obviously did, then you learn a lot, even though it will not thrill most synthetic chemists because this would be comparable to building a highway for an architect. I mean, it’s important, but it’s fairly dull compared to [building] the Guggenheim Museum, for instance… ”

I also very much agree with his philosophy of trying out ideas and reactions, which applies to a lot of early-stage drug discovery research as well:

“If it’s neither explosive nor toxic, you should try it no matter what people tell you about it. It’s one or two steps, why not?”

Yes, indeed – and his relative lack of the sin of pride comes through in that quote as well. Prof. Stork leaves behind a huge legacy; chemistry students will be learning things that he taught us for a long, long time to come. He also trained a long list of chemists in his academic career, and considered this one of his greatest accomplishments. He did what he did extremely well, he led a long and productive life, and I would guess that everyone who knew him is sorry to hear of his passing. It would be hard to wish for more.

42 comments on “Gilbert Stork, 1921-2017”

  1. KtheKnight says:

    He will be missed.
    I heard him several times lecturing, about only met him once.
    I was on my way to a symposium in honor of late Art Schultz in 2000, who had done post-doc with G. Stork. At the train station only one cab was waiting for customers. I arrived first and offered the man following me to join me in the cab. He asked: “How do you know where I’m going, young man?”.
    “I’m an organic chemist, Professor Stork.” He smiled and we had a nice conversation on chemistry and people on our way to Rensselaer Polytechnic Institute. Of course, I paid. It was a honor for me to ride a cab with one of my heroes in chemistry.

  2. BJK says:

    I’m almost embarrassed with myself to have not known he was still alive. Even doubly so that I never invited him for a seminar to my graduate program so many years ago.

  3. Antonio Regla says:

    I am very fortunate to have met him at a seminar he gave at Iowa State University’s chemistry department in the nineties, where I as a graduate student, we had a nice little chat after the seminar and really could appreciate the high quality of human being he was, and enjoyed having met one of the great organic chemists of the twentieth century, may he rest in peace.

  4. GladToMoveToProcess says:

    I spent 2.5 years as a postdoc with him. He changed my life. RIP, Gilbert.

  5. THUD says:

    Very sad news! Another true giant has gone on. I have known Gilbert
    personally for many years. Always a gentleman. He should have received the
    Nobel Prize long time ago for his enamine work. We are running out of
    chemists of his quality.
    Did you know he did his undergraduate work at UF in Gainesville? As the
    story goes he got off the bus, went to the department and asked for
    admission and a full private lab so he could do his own research. Very
    unusual and wonderful person and, of course, an outstanding chemist.

  6. Uncle Al says:

    the heroic age of organic synthesis” A small fraction of budget should be allocated for screwing around (weekends), to discover stuff. A vital lab reaches out as well as hunkers down. AI threatens to be marvelously creative “outside professional trajectory.”

    A Gabriel amine synthesis once gave me an epoxide in good yield. Interesting, though not for that first NMR – WTF!

  7. Michael TD says:

    Sorry to hear Prof. Stork’s passing. I was a chemistry Ph.D. student at Columbia in the 80’s. First thing comes to my minds after all these years, Prof. Stork seemed to always walk those squeaky stairs in the Chandler to his 6th floor office while young (and lazy) turk like us waited impatiently at 3rd floor for the elevator. RIP, Prof. Stork.

  8. Chris Dockendorff says:

    Jeff Seeman’s collection of anecdotes you linked to is hilarious– too many of us clearly take ourselves too seriously, and Prof. Stork clearly was not guilty of that sin. My lab does a lot of enamine chemistry, and his work is still highly relevant for us today. I’m always disappointed when a graduate student isn’t familiar with Stork’s enamine alkylation. Sorry to see such a luminary moving on, but grateful for his many contributions to organic chemistry.

  9. Dr. Nanaji Arisetti says:

    It is really bad news for all chemists, that we lost him. Still I am crazy about his enamine reaction. Gave us lot of scientists. RIP, Prof. Gilbert Stork

  10. one_man_CRO says:

    this is from the chem dept at columbia. a truly class act of a guy
    “We are sad to inform you that Professor Gilbert Stork passed away peacefully at 2:30pm, Saturday, October 21, 2017. He saw his last paper, “Synthetic Study toward the Total Synthesis of (±)-Germine: Synthesis of (±)-4-Methylenegermine” published in Organic Letters two weeks earlier. Work on the synthesis of germine began in 1979 and 15 students worked on the project through the year 2000. In 2010, Gilbert and his wife, Ayako Yamashita, decided that finishing the synthesis of germine would be a good retirement project. Working side-by-side (but only half time) in a small laboratory at Columbia, the two of them completed the synthesis of (±)-4-methylenegermine as a labor of love – a gift to each other and to all of Professor Stork’s students.”

    1. anon says:

      Heartwarming…

  11. Great organic chemist, RIP, knowing that has done enough humanly possible in this field of labor intensive.

    Some one mentioned about his wife- Heard that she was his former postdoc; Is that true? Best posdoc ever, if it is so!

  12. Tin Yau Chan says:

    It’s my great luck, joy and honor to be his last graduate student. He was a great scientist and most important of all a great person. He taught me so much in chemistry as well as treating people fair and right. He will be missed forever.

    1. Derek Lowe says:

      Very glad to hear from you!

  13. Chengzhi Zhang says:

    Thank you very much, Derek for the article.

    I was so sorry to hear that Professor Stork passed away. This is a great loss for Organic chemistry, for his students / postdocs (whose life being touched and changed for many of them!). I was fortunate enough to be in his lab during 1993-1994 as a postdoc, discussing chemistry in front of the chalkboard in his office at the 6th floor of Chandler building, repairing vacuum pumps, the once a year group skiing. But most of all I learned how to approach and solve problems. After getting knows Professor Stork, then you would not be surprised by the fact how many of his students / postdocs working in academics. He is a true gentleman and one of greatest chemist. There are not too many examples of the combination of the two.
    Another added benefit to work in Stork’s lab is to hear or clarify some very interesting stories, such as Stork once put himself in the ozonizor (No he didn’t. But he did put his thiophenol contaminated suit into the ozonizor in order to get rid of the smell for his evening award ceremony at Columbia), things like the inventor of Borch reduction (NaBH3CN), Dr. Borch is practicing medicine rather than chemistry (Borch got his MD while being a chemistry professor)………………………………..
    Professor Stork will definitely be remembered! May he be rest in peace!

    1. MTK says:

      The ozonizer story may be one of the funniest things I’ve ever heard. The story I heard is that he figured by oxidizing the thiol much of of the stink would be eliminated. Unfortunately, there was a side reaction, the oxidation of the fabric itself, resulting in the tattering of the suit itself as the evening went along leaving him in near rags by the end.

      I really don’t care if the story is true or not, it’s funny.

    2. The version I heard was that Gilbert and Frances Hoffman were perusing some chemical samples on the 6th floor, just before a fancy dress event at Columbia, and a few drops of a volatile sulfide spilled on Frances’ garment (not Gilbert’s suit). Frances was beside herself at the outcome, but Gilbert promptly devised a solution – he went down the hall and filled a balloon with ozone from the O3 generator, then played the ozone stream across the soiled area of the garment and, voila!
      This version didn’t have the garment disintegrating during the fancy event, but that it did not survive intact through the subsequent dry cleaning

      1. Barry says:

        Anyone who has actually used ozone will balk at the idea of a balloon filled with the stuff. Stork certainly knew how rapidly ozone eats rubber.

  14. Fred Ziegler says:

    Most saddened to hear of Gilbert’s passing. He was a remarkable inspiration as a teacher and mentor for me and many others. His spirit, stories and escapades in the laboratory will not be lost on those who knew him.

  15. MTK says:

    Let’s not forget umpolung chemistry also as a contribution.

    There was also the one time as a postdoc where I was trying to demonstrate a synthetic strategy via a total synthesis, but most of the steps were just to get to the key step more than anything.

    My advisor than cited me for violating “Stork’s Rule” as he called it. “The starting material should never be more difficult to make than the final product.”

    I don’t know if that’s really a rule Stork formulated, but it’s pretty darn good.

    1. MTK says:

      Oh wait. Umpolung was Seebach, right? My bad.

  16. Jacob From Upstate NY says:

    I was a graduate student (briefly) at Columbia back in 2001. Shortly after I started there, my undergraduate research professor, who had been a student of Stork’s, mailed me a proof of the last paper (which had gotten the cover of the journal it was published in) he had published with stuff that I had done, and he stuck a note in the envelope saying that if I ran into Prof. Stork, I should give him regards.
    So, I’m busily photocopying the cover proof and in walks Prof. Stork. Here I am, some brand new first year graduate student, and I go over to him, introduce myself, and say that his former student sends regards. Prof. Stork asked me what he was up to, and so I showed him the paper and the cover. He looked them over gravely, said “so that’s what has become of Hugh”, complemented me on my work, and wandered off about his business.
    And then I left Columbia, and that was that.

  17. RBW says:

    A giant of organic chemistry, and a perfectionist. Many projects were unpublished as he kept fine tuning and coming up with improvements. Better than Woodward at inventing new and general methodology whereas Woodward was master of creatively applying known transformations.

    1. Wavefunction says:

      I guess Woodward was more like Mozart, Stork and Corey are more like Beethoven.

  18. Clayton Heathcock says:

    Gilbert recruited me as a postdoc when he was teaching a summer course in Boulder in 1962. I told him I couldn’t do it because I was going to go to Berkeley and postdoc for Wendell Stanley. He said why don’t you come work or me and I’ll get you a faculty job at Berkeley. So I did and he did. I was there for year, 1963-1964, he completely shaped my future career. I have always remembered his philosophy about high-risk, high-reward ideas — “if it can be done in a day and it’s not dangerous, you should try it.”

  19. Tin Yau Chan says:

    Anyone interested in Prof. Stork’s story should read Frances Hoffman’s account in Aldrichimica Acta 1982 vol. 15 p. 3-12. I would like to add a few things learned from him over the years. Saturday afternoon is the best time to read in the chemistry library (even in the era of SciFinder because one can read something in addition to the target article and pay attention to the footnote). Of course, all the students and faculties knew that was the best time to find Prof. Stork. His attention to details in literature was most impressive. He could remember most of the reactions conducted by his students and postdocs. His love of teaching was amazing too. He could walk into the classroom bear hand and present an hour of organized lecture on the chalk board. I remembered one day he wanted to teach me how to use Science Citation Index (that was way before SciFinder). He just jogged in snow across the campus from the chemistry library to the engineering library. Potassium carbonate has very high solubility in water (at least 1:1 w/w). The saturated solution has such a high ionic strength that it can even salt out methanol in water. He was also very fond of new technologies. The best time to neutralize unused alkylating reagents (BuLi or Grignards) is to add them to dry ice in acetone. His lab was like a Christmas toy store for chemists. He was probably the first one install spinning distillation column, temperature programmable GC, RP-HPLC with radial compression columns and oligonucleotide synthesizer (that’s for making silicon backbone DNA). He was also the only senior faculty member to attend the CAS-ONLINE training. On the non-scientific side: one can tip restaurant servers any time, does not wait until paying the check. Always bring an object with the hotel’s address in a foreign city (he had the story of climbing up a traffic police stand to ask for direction in China).

  20. I am deeply saddened to learn that Gilbert Stork is gone.
    I was a graduate student in the Stork labs from 1975 until 1980, and it was the most exciting and challenging and transformative period of my life. After interviewing potential mentors at the major Eastern schools, I was drawn to him because he inspired creativity and drive, and an almost playful intellectual approach to solving problems, while the other big hitters mainly inspired fear and/or worship. Following time in academia, industry, and contract research, I left the laboratory and started a medical/technical translation practice, but the teachings from this master have always enlightened my approaches to work and to life, and continue to do so.
    I last saw him in May, 2004, when we met for lunch in NYC and I updated him on what I was up to. As so often in the past, I had brought him a problem to consider, this time of a linguistic nature: “peanut” as a food ingredient is sometimes called “arachide” in French, and sometimes “cacahuète” – why two different words? He pondered for a moment, and then replied that cacahuète is the count noun, referring to the individual peanuts, while arachide is the mass noun, used for peanut butter, peanut oil, etc. An elegant answer, and completely in character!
    Gilbert’s character was also such that his creativity knew no boundaries. On the subject of nut products, he told me that he had devised a method that could be used by immigration authorities to distinguish between North Americans and Europeans based on their reactions to two nut-based products: peanut butter and Nutella (a hazelnut butter, well known in Europe). On being fed a spoonful of each product, the North American would enjoy the peanut butter but gag on the Nutella – the reverse would be true for a European. Thus, despite false passports and accents, a continent-specific differentiation was possible. However, I don’t know if this project ever got out of development.
    We have lost a giant of science and, unlike some others of equivalent stature, one who was never enamored of being considered a giant. He guided many to become creative problem-solvers in his fashion, occasionally in spite of themselves. Those of us whose lives he shaped must all now feel like orphans, still with the enjoyable memories of scientific adolescence for comfort.

  21. Magrinho says:

    Great chemist, great person. RIP

    Columbia held a Symposium to commemorate his 70th birthday. Of his hundreds of former colleagues, grad students and post-docs, I believe only 3-4 did not attend and they sent sincere regrets.

    No words could do him more honor.

  22. Anubhav Narula says:

    Among thousands and thousands of teachers that have come & gone in this world, it is very rare that a spirit like Prof. Gilbert Stork come’s in a person’s life that would transform, uplift, stimulate, inspire them to a journey of their own to excel & discover their own god given hidden potential for their own good & society. Those who had the privilege & fortune to spend 2-5 years of their graduate or post- doc studies & research know how remarkable, humble and iconic human being, Prof. Stork was. You will not find a single soul that worked with Prof. Stork that was not impressed by his intellect, wisdom, and generosity. A true test of a great human being !!

    Prof. Stork was a globalist when it comes to education and spreading knowledge before it became fashionable in the field of commerce. Hundreds of students and post-docs from all over the world benefitted from the magnetic and spiritual personality of Prof. Stork. Even in his 90’s he had an amazing passion for learning. A few years back, I received a call and when I picked up the phone, he replied this is Prof. Gilbert Stork, I immediately became respectful and I said what can I do for you, sir. He replied, Anubhav, I have made a new $cent Molecule and he would like to send it to me for fragrance evaluation by IFF perfumers. Such was his passion, mind you he was 93 years old at that time. I am eternally grateful to Prof. Stork as without his guidance and assistance, I would not be working at IFF. He would always be alive in my memory as long as I am alive. May god bless his soul and rest it in peace and continue to bless his family for posterity. A true legend of chemistry has gone and left his mark for eternity.

  23. Jan says:

    He was from the hayday of ” like, lets treat our students like garbage and see if it makes them into superman or something”. Hopefully in another decade the last of that will be wiped out from science culture.

    1. Wavefunction says:

      To be honest, I think he was one of the better ones when it came to treating students and postdocs with decency.

  24. Scott says:

    While my Dad would say that Prof Stork “failed retirement” by going back to work (or never really quitting), I don’t think you can ever really retire from your passion. And it’s obvious to me that chemistry was his passion, even though I’m nowhere near a chemist (HR degree for the record. I visit here for the various things Derek Lowe won’t work with).

    I wonder what kind of interesting chemistry will get done at the wake?

    1. Anonymous says:

      “I don’t think you can ever really retire from your passion.” Without tenure, you are FORCED to retire from your passion. And the sequestration of literature access behind paywalls makes it worse and worse.

  25. BOB says:

    Sad news.

    I remember interviewing at Columbia and happening into an elevator with the late great GS. He asked me what I wanted to study at Columbia and I replied organic synthesis. With a little smile and wink he responded: “Me Too.”

    A gentleman and a scholar, he will be missed…

  26. tangent says:

    I like this one:

    “II used to make diethylaluminum cyanide myself, and I usually liked to do it on December 31st because it’s my birthday, and it was a sort of black humor that, if I died on that day, it would be easy to tell how old I was. And so I would do it. In fact, I sometimes did it in a tuxedo, which was really some ridiculous operation.”

  27. CU alumnus says:

    Sadly, Columbia’s Chemistry Department suffers another great loss. Ronald Breslow passed away yesterday.

    1. Hap says:

      Wikipedia (https://en.wikipedia.org/wiki/Ronald_Breslow) says this as well, but I couldn’t quickly find any other source.

      1. Hap says:

        And this, but I don’t know where the Baran group heard: https://twitter.com/BaranLabReads/status/923525799961088000

  28. Wavefunction says:

    Breslow is sadly the fifth pioneering chemist to have passed away during the last year.
    http://wavefunction.fieldofscience.com/2017/10/a-terrible-year-for-academic-organic.html

  29. SteveT says:

    I was a grad student with Koji Nakanishi at Columbia from 1974 through early 1979. With Koji I was doing total synthesis and Koji would say to me “If you need help with this I can’y help you, you need to go and talk to Gilbert”. So I would trek from the 3rd to the 6th floor of Chandler to speak with Professor Stork about synthetic strategy, reaction nuance, alternatives, etc. He was very generous with his time and advice, opening up his thought process for you, allowing you to see how he approached a problem. He would say “you could do this, no you don’t want to do this because…” or you could do that – that is a good thing to consider because…”. The willingness to let you see how he approached a problem in depth was usual and could be directly attributed to his desire to be a TEACHER. I have applied these notions throughout my career in academia and in the pharmaceutical industry. Prof. Stork used that same interesting “you could – no you don’t want to” and “you could – that would be a good idea” approach when I asked him for some advice about selecting a post doc. I had the good fortune to continue to visit with him through the 90’s and into the early 2000’s when I would go recruiting – I vividly remember the puzzled look on his face when I asked him to sign a baseball for me – telling him it was for my Chemistry Hall of Fame. My son had the opportunity to get to know Prof. Stork a bit while doing a post doc with Jim Leighton – he would then ask me about the “old days”. I’ve given my son a snapshot of the world of synthesis in the form of my Stork synthesis course notes from 1975. This was accompanied by a description of a teaching technique used by Prof. Stork – when a question was posed he would often turn to the board – draw a 6 membered ring – rapidly erase it – and answer the question.

  30. Rustum Boyce says:

    there is so much to remember, his ever friendly smile, his sense of humor and heavy European accent, is indomitable spirit!he was a common sight in the library pouring over JACS and reference books in the library after 10 PM ! I think he provided much of the mojo to Columbia chemistry for 1/2 a century! I will always treasure my chem exams graded by Prof. Stork.

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