Asymmetric Total Synthesis of a Pentacyclic Lycopodium Alkaloid: Huperzine‐Q
- 12 July 2011
- journal article
- research article
- Published by Wiley in Angewandte Chemie International Edition
- Vol. 50 (35) , 8025-8028
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.Keywords
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