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Review | Regular issue | Vol 57, No. 7, 2002, pp.1327-1352
Published online, 1st January, 1970
DOI: 10.3987/REV-01-542
Syntheses of (-)-Physostigmine, with Particular Emphasis upon the Clarification of Two Enigmatic Early Synthetic Approaches

Brian Robinson

*Millhaven, Tideswell Lane, Eyam, Derbyshire, S32 5RD, U.K.


Following a synopsis of the studies whereby the structure, including absolute configuration, of (-)-physostigmine - a metabolite from diverse botanical and also microbial sources - was established, the pharmacology and clinical uses of the alkaloid, its enantiomer and its hydrolysis product, (-)-eseroline, are briefly but comprehensively discussed. Synthetic approaches to (-)-physostigmine and its 1,2,3,3a,8,8a-hexahydro-3a-methylpyrrolo[2,3-b]indole ring system are then considered, with particular emphasis upon the early endeavors in this area by three independent groups and the interpretation of the results obtained by one of them.