Synthesis of (-)-Lycopodine

H. Yang; R. G. Carter; L. N. Zakharov

doi:10.1055/s-0028-1087235

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Synfacts 2009(1): 0007-0007
DOI: 10.1055/s-0028-1087235

Synthesis of Natural Products and Potential Drugs

Synthesis of (-)-Lycopodine

Contributor(s): Philip Kocienski
H. Yang, R. G. Carter*, L. N. Zakharov
Oregon State University, Corvallis, USA

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Publication History

Publication Date:
18 December 2008 (online)

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Significance

An asymmetric synthesis of (-)-lycopodine by Carter and co-workers was based on sequential intramolecular Michael addition and Mannich reactions. A rare 1,3-transposition of an allylic sulfone was observed in the Zn(OTf)₂-catalyzed Mannich reaction transforming imine D to the tricycle H.