Total syntheses of (-)-huperzine Q and (+)-lycopladines B and C

Abstract

Utilizing a late-stage enamine bromofunctionalization strategy, the twelve-step total synthesis of (-)-huperzine Q was accomplished. Furthermore, the first total syntheses of (+)-lycopladines B and C are described. An unprecedented X-ray crystal structure of an unusual epoxyamine intermediate is also reported, and the synthetic application of this intermediate in natural product synthesis is demonstrated.

Keywords: alkaloids; epoxyamines; metathesis; natural products; total synthesis.