From Decades to Minutes: Steps Toward the Structure of Strychnine 1910–1948 and the Application of Today's Technology

Abstract

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The Relationship of William Henry Perkin, Jr. and Sir Robert Robinson: Teacher and Student, then Student and Teacher

“…Table 1 also lists Robinson's number of publications with and without Perkin as a co‐author, for all Robinson's publications and for just his strychnine papers. Lastly, to place the story of the structure determination of strychnine [49–51] in some perspective, related information is presented for R. B. Woodward.…”

“…Recall that it was during the very period of collaboration with Perkin that the great rivalry between Robinson and Ingold mushroomed, primarily hosted by and within Robinson [95–97] . And we also know of the great rivalry between Robinson and Woodward in the late 1940s and early 1950s dealing with the structures of penicillin [98] and strychnine, [49, 99] and then the total synthesis of steroids [100] . Thus, Robinson was exquisitely capable of championing relentless competition.…”

“…I thank Dean Tantillo with whom a joint project on the structure determination of strychnine was undertaken [49] and which stimulated the research upon which this paper is based. I thank Peter Morris, Ian D. Rae, and Anthony Travis (for pointing out the Chaim Weizmann reference) for very helpful discussions and the staff of the Boatwright Memorial Library, University of Richmond, for their technical support.…”

Diverse Views in the Assignment of Credit for Research Discoveries

“… 11 − 13 Several examples of Robinson’s proposed structures for strychnine are shown immediately below. 11 …”

An Asymmetric Synthesis of (+)-Isostrychnine Based on Catalytic Asymmetric Tandem Double Michael Addition

“…The Strychnos alkaloid is a subset of the indole alkaloid with a common cyclohexane-fused spiro­[pyrrolidine-3,3′-oxindoline] framework (A/B/C/E rings) and a characteristic bridged piperidine ring (D-ring, Figure ). Strychnine, one of the most complex and famous Strychnos alkaloids, possesses seven rings, including additional tetrahydrooxepine (F-ring) and piperidin-2-one skeletons (G-ring). After its first isolation in 1818, the structure of strychnine was not fully elucidated until 1946 .…”