A short enantioselective total synthesis of the fundamental pentacyclic triterpene lupeol.

J Am Chem Soc

Department of Chemistry and Chemical Biology, Harvard University, Cambridge, Massachusetts 02138, USA.

Published: October 2009

The first enantioselective synthesis of lupeol has been developed by applying two carefully crafted cation-pi cyclization stages to generate the pentacyclic structure with complete stereocontrol. The synthesis (Scheme 1) is noteworthy because of its brevity and also because it solves a longstanding problem in the field of natural product synthesis.

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Source
http://dx.doi.org/10.1021/ja906335uDOI Listing

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