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Total Synthesis of (±)-Gelsemine
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1999
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Diversity Oriented SynthesisEngineeringComplex Molecular ReorganizationTotal SynthesisOrganic ChemistryNew Total SynthesisChemistrySynthesis MethodMannich CyclizationSynthetic ChemistryEnantioselective SynthesisBiomolecular Engineering
A complex molecular reorganization (1-->2), a sequential anionic aza-Cope rearrangement and Mannich cyclization, and an unprecedented intramolecular Heck reaction of the tetrasubstituted double bond of a vinylogous carbamate are key steps in a new total synthesis of (+/-)-gelsemine (3). MOM=methoxymethyl, DBU=1,8-diazabicyclo[5.4.0]undec-7-ene.