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Synfacts 2006(6): 0543-0543  
DOI: 10.1055/s-2006-934494
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Tarchonanthuslactone

Contributor(s): Philip Kocienski, John Cooksey
M. S. Scott, C. A. Luckhurst, D. J. Dixon*
University of Cambridge, UK
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Publication History

Publication Date:
19 May 2006 (online)

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Significance

Tarchonanthuslactone is a plant metabolite isolated from Tarchonanthus trilobus that lowers blood-plasma glucose in diabetic rats. In this total synthesis the Dixon group demonstrates the use of a highly enantioselective catalytic reduction of an N-acyl pyrrole to control the absolute stereochemistry and direct a highly diastereoselective syn-selective reductive cascade to install all the stereocenters present in the natural product.