Enantioselective Synthesis of Yohimbine Analogues by an Organocatalytic and Pot-Economic Strategy

An efficient and one-pot method has been developed for the enantioselective synthesis of pentacyclic indole derivatives with the yohimbane skeleton via a sequence of asymmetric Michael–Michael–Mannich–reduction–amidation-Bischler–Napieralski–reduction reactions with a high diastereoselectivity and high enantioselectivities (up to >99% ee). The seven-step reaction sequence, which generates five bonds and five stereocenters, can be conducted with a pot-economic synthetic strategy and one-pot operation in good yields. The structure and absolute stereochemistry of two products were confirmed by X-ray crystallography analysis.