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Synfacts 2006(3): 0194-0194  
DOI: 10.1055/s-2006-931930
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York

Synthesis of (-)-Vindoline

Contributor(s): Philip Kocienski, Thomas Snaddon
Y. Choi, H. Ishikawa, J. Velicicky, G. I. Elliot, M. M. Miller, D. L. Boger*
The Scripps Research Institute, La Jolla, USA
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Publication History

Publication Date:
21 February 2006 (online)

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Significance

Boger and co-workers employed a tandem Diels-Alder/[3+2] cycloaddition cascade sequence to efficiently construct densely functionalized pentacyclic scaffold (±)-E en route to Vindoline. This remarkable sequence encompasses four C-C bond constructions with concomitant formation of three rings and six stereocenters, three of which are quaternary. For the synthesis of enantiopure Minovine via a similar strategy see: D. L. Boger et al. Org. Lett. 2005, 7, 741-744.