Obituary Chemie

Angewandte Obituary Chemie and aspidospermine, as was radical cyclization in Gilbert Stork (1921–2017) the construction of seychellene, patchouli alcohol, and prostaglandin F2a. Master of Organic Synthesis Stork was born in Brussels, Belgium on Decem- Professor Gilbert Stork died on October 21, 2017 at ber 31, 1921, and moved with his family to the the age of 95. He trained multiple generations of United States in 1939. He earned his BS in 1942 synthetic organic chemists and inspired them with from the University of Florida, and his PhD in 1945 his passion for chemistry, with his remarkable from the University of Wisconsin under the guid- creativity, and, most importantly, with his humility ance of Prof. Samuel M. McElvain. His thesis work and warmth. He had a keen aesthetic sense and a focused on quinine, with which he apparently fell in deep appreciation of art. He will be remembered as love while in college (and eventually synthesized in one of the greatest practitioners of the art of 2001). In 1946, he took a position at Harvard Gilbert Stork organic synthesis. University, where he proposed the Stork–Eschen- Each of us was privileged to be a member of the moser hypothesis for the biosynthesis of terpenes Stork group. For over sixty years, the Stork through polyene cyclization, and achieved the laboratory at Columbia University was legendary stereospecific synthesis of cantharidin. He moved as an unmatched environment for the study and to Columbia University in 1953, and became practice of organic synthesis, a reflection of the professor in 1955 and Eugene Higgins Professor extraordinary qualities of Gilbert Stork. His enthu- in 1967. His illustrious career was recognized with siasm and energy were both contagious and inspir- numerous honors and election to many academies ing, and, to us and to the entire chemical commun- and learned societies. ity, he provided the consummate example of how to Stork became professor emeritus in 1993, and do research and how to mentor students through for the next twenty-four years continued to pursue his unique combination of scientific brilliance and his passion for research, publishing on 12a-deoxy- personal kindness. tetracycline, digitoxigenin, quinine, reserpine, His career was remarkable for the breadth and taxol, oligonucleotides, b-mannopyranosides, depth of his contributions to organic synthesis, from patchouli alcohol, morphine, codeine, and the- the landmark synthesis of cantharidin (1953), which baine. His final publication described the synthesis was arguably the first example of a planned stereo- of 4-methylenegermine, the culmination of a forty- specific total synthesis, to the recently reported year project with sixteen co-authors including his synthesis of 4-methylenegermine. Over the course wife, Dr. Ayako Yamashita, with whom he com- of this extraordinary seven-decade career, he pleted this final project. achieved landmark successes in the total synthesis We and so many others in the chemical of virtually every natural product class: terpenes, community fondly remember Storks sense of alkaloids, prostaglandins, macrolides, and tetracy- humor, his charm, and his zest for life. His wit clines. Each of these syntheses is characterized by and warmth were very much on display in a its simplicity and beauty. During the execution of footnote in his last paper (published just six these synthetic masterpieces, he developed a series weeks before his passing): “At this point, we of methodologies that became central to the realized that we did not have enough material (a practice of organic synthesis, including the use of few milligrams) to go through the several steps for enamines and enol silyl ethers and the stereo- this (final) conversion. One would have to restart selective generation of enolates by dissolving-metal the whole synthesis. But I (G.S.) am now 95 years reduction. His synthesis of prostaglandins from old …” (Org. Lett. 2017, 5150). glucose was one of the earliest and most elegant On behalf of all of Storks former students and examples of the use of starting materials from the postdoctoral research associates, and colleagues “chiral pool”. He was also a trailblazer in the around the world, we express our deepest appre- renaissance in radical cyclization chemistry that ciation for his influence on the world of chemistry continues to this day. and on all of our lives. The most unique feature of Storks now classi- Eiichi Nakamura cal work in the total synthesis of natural products The University of Tokyo, Tokyo (Japan) was that these syntheses were not solely about the Jeffrey D. Winkler completion of the target, no matter how complex, University of Pennsylvania, Pennsylvania (USA) but also about what was learned en route. Profound Varinder K. Aggarwal insights into basic reactivity and the development University of Bristol, Bristol (UK) of new synthetic methods were prizes that he joyously coveted along the way. The power of the methodology that he developed was showcased International Edition: DOI: 10.1002/anie.201711474 beautifully in the application of enamine chemistry German Edition: DOI: 10.1002/ange.201711474 in his elegant syntheses of lycopodine, yohimbine, &&&& 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim Angew. Chem. Int. Ed. 2017, 56,2.

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