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Synfacts 2010(1): 0018-0018  
DOI: 10.1055/s-0029-1218403
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of Vannusal B

Contributor(s): Philip Kocienski
K. C. Nicolaou*, A. Ortiz, H. Zhang
The Scripps Research Institute, La Jolla, USA
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Publication History

Publication Date:
21 December 2009 (online)

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Significance

A key step in the synthesis of vannusal B is the reductive cyclization of the allylic carbonate D initiated by reduction of an aldehyde with SmI2. Remarkably, both of the nascent stereogenic centers at C10 and C28 had the correct stereochemistry.