Gilbert Stork: in his own words and in the musings of his friends.

s 1945, 39, 2991(5). Figure 7. Carl Djerassi, learning how to drive a tractor in Tarkio, Missouri, 1941. Photo courtesy C. Djerassi. . Angewandte And Finally 3014 www.angewandte.org 2012 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim Angew. Chem. Int. Ed. 2012, 51, 3012 – 3023 “And then, as I just had thrown it in there, and it fumed furiously and red fumes of who knows what, nitrous oxide of various kinds were being produced there. I became frantically concerned because fat is glycerides. So, I m hydrolyzing the fat to glycerin. You make nitroglycerine by taking glycerin and nitric acid and sulfuric acid, and obviously, I m going to produce a pile of nitroglycerine and blow up the entire building with my steak. “Now, what is an interesting point there, why didn t it? And of course, the reason is kinetics. That is, the kinetics of oxidation of the glycerol at that temperature is much, much, much, I mean, infinitely faster than the cold temperature nitration of glycerin. And so the place was safe.” [16] Chemistry on One’s Birthday “I 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.” [16] Gilbert’s Experimental Prowess As told by Derek Barton*: “When I arrived at Harvard in 1949, Gilbert was working with his own hands on the synthesis of morphine. This was an ill-advised activity. Gilbert had, and still has, a brilliant mind. However, its extension to the control of his hands was somewhat lacking, so he did not accomplish very much until his first graduate students arrived... ” Why Synthesis? “The origin [of my passion for synthesis] is the structure, and the structure needs methods. Not the method first and then the structure. Structure, problem, method, back to structure. It s kind of a sculpture. It s a challenge. Everybody gets interested; as soon as you can make a problem of something, it becomes interesting. Whether you re a chess player, or whether you try to find a way of preventing paper bags from falling apart when they re wet. If you can make it into a problem, it becomes interesting.” [1] The True Meaning of Success in Organic Synthesis “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... ” “So something could be not terribly glamorous but extremely important, or vice versa. I think that B12 was vice versa. It s enormously complicated.” [1] The Core Essence of Organic Synthesis “I finally think I understand why people play golf. Why are they so fascinated by golf? If you really want to put that ball in that hole, there are many other things to do that. And the reason, of course, is that no one interferes with you. You re 100% responsible for what you do, right and wrong. And so it s nice. If you play team sports, well, maybe somebody didn t pass the ball to you at the right time... “You can see why [individually focused activities] would make you passionately involved.... in synthesis because you can devise any scheme that you want... it s also easy to do, in the sense that if an experiment doesn t work, you just throw it out... it doesn t take a year to do an experiment. In fact, that s the beauty of synthetic organic chemistry still. You can think on the weekend a great idea and, if you re really motivated, you go over the weekend and try it, and you can know at the end of that day that thing is no good... And so, it is both easy and very frustrating. So is golf. I mean, it s easy to hit that ball with a stick... ” To Explore, Not To Sleep “Most of my students have been graduate students. And these are students who are pretty well committed... You don t really have to instill enthusiasm for chemistry that much, it s already there. You have the problem of not killing it all together. They may not have the courage to try things. They Figure 9. Stork at Colombia University, 1997. Photo courtesy J. I. Seeman. Figure 8. Stork as