Angewandte. And Finally DOI: 10.1002/anie.201200033 Gilbert Stork Gilbert Stork: In His Own Words and in the Musings of His Friends** Jeffrey I. Seeman* “The absent-minded but organized Gilbert Stork… ” can be found in Gilberts two recent reviews.[4,5] He was not just Koji Nakanishi[2] a synthesizer of numerous important natural products; he was a major developer of methodology that sustains the exper- “Stork is as nice as they come. Few people of his brilliance imental work of the bench chemist! The Stork enamine are so completely free from any conceit.” reaction and his radical cyclizations are just two examples of Louis F. Fieser[3] his major methodological contributions. I am both a fan and a friend of Gilbert. I have long been Born in Brussels, Belgium on December 31, 1921 and for involved in studying his research and life, first as a student in 59 years a professor at Columbia University, Gilbert Stork is need of synthetic methodologies for my graduate research[11] one of organic chemistrys most beloved and simultaneously and later, much later, as a historian of chemistry (Figure 1).[12] eminent artists.[1–3] His creativity extends far beyond his chemical successes. He has a special way, an aura that is and has been unique in our community of scholars and—yes— unique among a group of already rather eccentric practitioners. Many celebrations highlighted 2011, the International Year of Chemistry. Some of these honored Gilberts reaching the wonderful age of 90. See, for example, Gilberts own recol- lections[4] published in an issue of Tetrahedron honoring his 90th birthday and in a broad review of his chemistry published a decade ago.[5] The reader is urged to read Gilberts own articles. Why so much attention on Gilbert Stork? It is because Gilbert has been one of the leaders of synthetic organic chemistry for decades. He has propelled the discipline of Figure 1. Seeman and Stork examining the R. B. Woodward collection organic chemistry throughout the broader community of at the Harvard University Archives, August 2009. chemists by virtue of his research and scholarship, his legacy of graduate students and postdoctoral fellows, and his demeanor. Stork is not only one of the most esteemed and (I might still be in graduate school had it not been for the Stork well-liked of chemists; he has mentored a cadre of some of the enamine reaction.[13,14]) Thus, I wanted to make some special disciplines most successful organic chemists whose loyalty to contribution toward the celebration of Gilberts life. What and even reverence for this fine gentleman is extraordinary. As better way, I realized, then assembling and sharing Gilberts stated by one of his former students, “Gilbert is a global own words and deeds. So, what follows is mostly a collection of treasure! He has directly and indirectly inspired a legion of “Storkisms”. They—and he—are often funny and always scientists who have gone on to make profound contributions to insightful. These snapshots contain lessons in life. Enjoy, thank science, health care, medicine, materials, the economy, educa- you Gilbert, and Happy Birthday! tion and our quality of life.” Arguably, his synthesis of cincholoipon (1946)[6] was the Except as noted below, all the quotes are by Gilbert Stork first planned stereocontrolled synthesis, and cantharidin himself. (1951[7]) was probably the first natural product synthesized with high stereoselectivity. These early successes were book- ended by the first stereoselective synthesis of quinine (2001)[8] Excitement of Science versus Making a and the syntheses of reserpine (2005)[9] and morphine, codeine, Contribution and thebaine (2009.)[10] Highlights of the fifty years in between “Some things actually gave us a great thrill, which are not particularly important. Some were important, but not that much. For instance, the prostaglandin synthesis from glucose [*] Dr. J. I. Seeman is a beautiful piece of work.[15] It was not all that important, Department of Chemistry, University of Richmond but in a way it sort of was one of the landmarks of establishing Richmond, VA 23173 (USA) E-mail: [email protected] that you can use the chiral sugar pool to make a complex chiral compound which is not obviously embedded within the [**] Dedicated to the memory of an astute historian of chemistry and one of the interviewers of Gilbert Stork’s 1991 oral history quoted glucose structure. There were others like this. They were just herein,[1] James J. Bohning, who passed away at the age of 77 on simply a thrill. Like solving a mathematical puzzle. You get a September 2, 2011. thrill, but it doesnt mean that youre necessarily making an 3012 2012 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim Angew. Chem. Int. Ed. 2012, 51, 3012 – 3023 Angewandte Chemie important mathematical contribution. But that one was a On Taking Tests [1] thrill.” “[As an entering undergraduate student at the University of Florida in Gainesville,] I was doing very well on the chemistry exams, which were a multiple choice thing, where I could test Painful Lessons of Life my hypothesis that the longest answer is statistically much “I went to what the French called a lyce which is sort of a more likely to be the correct one than the shortest one simply preparatory school for college …What the French system was because its harder to phrase correct things than incorrect based on at that time was essentially memory. Now, this is not things.” [1] a very reasonable system but they teach you resistance to pain because it was really extremely painful to learn the amount of material you were supposed to learn and also, a certain skill My Undergraduate Summer Job at getting around the painfulness of the system for survival “I had a job as a waiter in a private establishment just outside reasons. That probably has been very successful in fact. of [the University of Florida]. I remember when somebody in May have been the most important thing that I learned a crowded room full of school teachers ordered what was there.” [16] probably beer of some kind, and I thought they wanted watermelon. [laughter] I made my way with this big water- melon through this crowded room, and it was not the right Stork’s Childhood Naivet thing. Eventually I got fired from that job.” [1] “I was good at French literature, and I was even selected to represent my lyce in a nationwide high school competition in French writing. I was not terribly self-confident, however, and did not think that I could get a job in what I liked to do. So I On the Way to Graduate School: Slightly Older was actually considering getting some safe government Naivet “I decided to go to the University of Illinois [for graduate position. Something in French Indochina seemed especially school] because Roger Adams was there. Hard as it is to attractive to me. Things took a different turn. In 1939, my believe, I didnt realize that you had to apply for admission. father became very concerned about what was going to The idea that they wouldnt immediately give me a lab didnt happen in Europe and decided to emigrate [to the United [17] occur to me. I went to Illinois and demanded to talk to Roger States].” Adams. A secretary told me that he was busy and could not see me. I thought this was outrageous and took the train to [17] Nonconformist and Novel Problem-Solver Wisconsin… ” As told by Frances Hoffman[*]: “[Gilberts] creative solutions to difficult problems also surfaced early. Gilberts favorite Madison, Wisconsin occupation during his summers at Ostend was going for pony “I was quite happy in Mad- rides on the beach. Unfortunately, he often had to wait fifteen ison [for graduate school] to twenty minutes because of the long lines. One weekend, even though, when it was Gilbert was left in the care of his favorite Uncle Alex. Gilbert À208F, you get the acute explained his problem to his uncle and proposed that the way experience of having your to solve it was to have a pony of his own. His uncle found this scalp shiver—a strange to be a good solution, but when the pony appeared on the thing—if you dont wear grounds of his home, considerable rumblings from the the proper clothing. [laugh- neighbors mounted to a volcanic eruption when Gilberts ter]” [1] parents returned.” [18] Figure 3. Stork as a graduate student, Madison, WI, ca. 1944. On Overcoming the Diffi- Photo courtesy G. Stork. culties of Learning Giving Authorship to “The truth is, when you dont One’s Professor know a language, its easy for “I also did not know you were supposed to put your people to say, Well, you can professors name on your papers. It shows how tolerant [19] learn it. Its obviously true. At [Samuel M.] McElvain [Storks PhD advisor at Wisconsin] one extreme, you say, If one was. Most people would have been very upset. He flipped billion little Chinese can learn slightly, but not too much, when he picked up a JACS [in 1945] [20] Chinese, it mustnt be that and saw there was this communication, my first paper [that he knew nothing about]… McElvain said, You cut this Figure 2. Stork, ca. 1940. hard. Thats one point of Photograph courtesy G. Stork. view.” [1] fooling around out, and moved me next to his office. [laughter] Then I started working more seriously on [our [*] Hoffmann is a friend and colleague of Stork’s for decades, former joint projects]… [The end of that paper said, The work in this Director of Chemical Laboratories at Columbia University.