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Total Synthesis of (-)-Strychnine via the Wieland-Gumlich Aldehyde
Daniel Solé1, Josep Bonjoch1, Silvina García-Rubio1
1Laboratory of Organic Chemistry, Faculty of Pharmacy, University of Barcelona, Av. Joan XXIII s/n, E-08028-Barcelona (Spain), Fax: (+34) 93-4021896.
Abstract:
Fifteen steps suffice for an enantioselective total synthesis of (-)-strychnine (1) from 1,3-cyclohexanedione. The key steps are the easy generation of the enantiopure intermediate 2, the closure of the piperidine ring by a reductive Heck reaction, and the elaboration of the indoline nucleus in an advanced synthetic stage. TBDMS=tert-butyldimethylsilyl.
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