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Total Synthesis of (−)-Strychnine via the Wieland-Gumlich Aldehyde
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1999
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Asymmetric CatalysisNatural Product SynthesisEngineeringNatural SciencesDiversity-oriented SynthesisTotal SynthesisOrganic ChemistryFifteen Steps SufficeChemistryHeterocycle ChemistryPharmacologyPiperidine RingEnantioselective SynthesisBiomolecular EngineeringAdvanced Synthetic Stage
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.