No abstract

A bioinspired formal synthesis of montanine-type Amaryllidaceae alkaloid pancracine through selective hydrogenation of 3-aryl indole derivative is disclosed. The key features of the current synthesis include hexahydroindole synthesis via chemo-selective hydrogenation of aryl-substituted indole and a diastereoselective silyl hydride reduction of an iminium intermediate, which is generated from enaminone via Tf2O activation. The eight-step assembly of the 5,11-methanomorphanthridine framework represents a novel and efficient strategy that enables one of the shortest syntheses of pancracine so far.

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