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Synfacts 2008(2): 0118-0118  
DOI: 10.1055/s-2007-992509
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York

Synthesis of (-)-Membrenone B

Contributor(s): Philip Kocienski, Zofia Komsta
V. Jheengut, D. E. Ward*
University of Saskatchewan, Saskatoon, Canada
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Publication History

Publication Date:
23 January 2008 (online)

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Significance

(+)-Membrenone B was isolated from the skin of a Mediterranean mollusc Pleurobranchus membranaceus. It is a feeding deterrent for some of its natural predators. This concise synthesis focuses on two aldol reactions, using thiopyrans to control enolate geometry. A similar strategy was used in the synthesis of erythromycin: R. B. Woodward et al. J. Am. Chem. Soc. 1981, 103, 3210.