Highly Efficient Diastereoselective Michael Addition of Various Thiols to (+)-Brefeldin A

The Michael addition of thiols to brefeldin A occurs with high diastereoselectivity, affording ratios of major to minor diastereomers of at least 30:1. On the basis of the X-ray structure of a crystalline dibenzoyl derivative, the major diastereomers are assigned the 3R configuration, while the mino...

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Bibliographic Details
Published in:Journal of organic chemistry 1998-01, Vol.63 (2), p.273-278
Main Authors: Argade, Ankush B, Haugwitz, Rudiger D, Devraj, Rajesh, Kozlowski, John, Fanwick, Phillip E, Cushman, Mark
Format: Article
Language:English
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Summary:The Michael addition of thiols to brefeldin A occurs with high diastereoselectivity, affording ratios of major to minor diastereomers of at least 30:1. On the basis of the X-ray structure of a crystalline dibenzoyl derivative, the major diastereomers are assigned the 3R configuration, while the minor diastereomers have the 3S configuration.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo971292y