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Synfacts 2006(12): 1199-1199  
DOI: 10.1055/s-2006-955602
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York

Synthesis of (+)-Streptazolin

Contributor(s): Philip Kocienski
F. Li, M. J. Miller*
University of Notre Dame, USA
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Publication History

Publication Date:
22 November 2006 (online)

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Significance

Streptazolin is a very unstable metabolite of Streptomyces viridochromogenes. The key step in this synthesis is the use of a silicon-tethered ring-closing metathesis followed by a protodesilylation to afix the stereochemistry of the ethylidene side chain. The overall yield from aminocyclopentenol A was 4.8% (16 steps).