Asymmetric total synthesis of a pentacyclic Lycopodium alkaloid: huperzine-Q

Nakayama, Kogure, Kitajima, Takayama (2011) Asymmetric total synthesis of a pentacyclic Lycopodium alkaloid: huperzine-Q Angew Chem Int Ed Engl (IF: 17) 50(35) 8025-8

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.Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Links

http://www.ncbi.nlm.nih.gov/pubmed/21751323
http://dx.doi.org/10.1002/anie.201103550

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