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.