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Asymmetric total synthesis of a pentacyclic Lycopodium alkaloid: huperzine-Q
Atsushi Nakayama1, Noriyuki Kogure, Mariko Kitajima
1Graduate School of Pharmaceutical Sciences, Chiba University, Yayoi-cho, Inage-ku, Chiba, Japan.
Angewandte Chemie (International Ed. in English)
|July 14, 2011
Abstract:
Right on Q: the first asymmetric total synthesis of (-)-huperzine-Q, which possesses six stereogenic centers and a spiroaminal moiety, has been achieved in 19 steps and 16.4 % overall yield. This synthesis involved a novel stereoselective Pauson-Khand reaction, a vinyl Claisen rearrangement, and a biomimetic spiroaminal formation. TBDPS=tert-butyldiphenylsilyl.
