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Synfacts 2006(6): 0534-0534  
DOI: 10.1055/s-2006-934487
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York

Synthesis of (±)-Gelsemine

Contributor(s): Philip Kocienski, Fiona Black
W. G. Earley, J. E. Jacobsen, A. Madin, G. P. Meier, C. J. O’Donnell, T. Oh, D. W. Old, L. E. Overman*, M. J. Sharp
University of California, Irvine, USA
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Publication History

Publication Date:
19 May 2006 (online)

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Significance

In consecutive papers, a detailed account is given of the synthesis of (±)-gelsemine in 1.1% overall yield. The highly functionalized hexacyclic ring system is constructed using a base-promoted aza-Cope rearrangement-Mannich cyclization sequence and an intramolecular Heck cyclization. For the second paper in the sequence, see: L. E. Overman et al. J. Am. Chem. Soc. 2005, 127, 18054-18065.