Total Syntheses of (-)-Huperzine Q, (+)-Lycopladines B and C

Benke Hong, Houhua Li, Jinbao Wu, Jing Zhang, and Xiaoguang Lei*
Angew. Chem. Int. Ed. 2015, 54, 1011-1015

Utilizing a late-stage enamine bromofunctionlization strategy, we have accomplished a 12-step total synthesis of (-)-huperzine Q as well as the first total syntheses of (+)-lycopladines B and C. We also report an unprecedented X-ray crystal structure of an unusual epoxyamine intermediate and demonstrate its useful synthetic application in natural product synthesis.

Utilizing a late-stage enamine bromofunctionlization strategy, we have accomplished a 12-step total synthesis of (-)-huperzine Q as well as the first total syntheses of (+)-lycopladines B and C. We also report an unprecedented X-ray crystal structure of an unusual epoxyamine intermediate and demonstrate its useful synthetic application in natural product synthesis.