Abstract
Condensation of methyl 3-benzyl-1,2,3,4,5,6-hexahydroazepino[4,5- b]indole-5-carboxylate ( 3) with methyl Z-4-formylhex-3-enoate ( 6) gave cis-fused dimethyl 5-benzyl-4-ethyl-2,4a,5,6,7,12-hexahydro-1 H-benzo[2,3]azepino[4,5- b]indole-2,12b-dicarboxylate and its trans-fused diastereomer. Selective reduction of the less hindered ester group with sodium borohydride to an alcohol ester, tosylation, debenzylation, and cyclization gave racemic catharanthine ( 1).
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