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Synfacts 2009(12): 1310-1310  
DOI: 10.1055/s-0029-1218325
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart ˙ New York

Formal Synthesis of (-)-Cochleamycin A

Contributor(s): Philip Kocienski
S. Mukherjee, D. Lee*
University of Illinois at Chicago, USA
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Publication History

Publication Date:
20 November 2009 (online)

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Significance

Cochleamycin A is a Streptomyces metabolite with significant antibiotic activity against Gram-positive bacteria and cytotoxicity towards P388 leukemia cells. The key step in the synthesis of K, an intermediate in Roush’s synthesis, is an intramolecular ring-closing metathesis of the silaketal I to give the (E,Z)-diene J in ca. 61% yield.