Total Synthesis of (−)-Strychnine via the Wieland-Gumlich Aldehyde

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.