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Issue 28, 2016
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Enantioselective synthesis of (+)-brevipolide H

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Abstract

The enantioselective synthesis of natural brevipolide H is reported for the first time. By way of Sharpless epoxidation of penta-1,4-dien-3-ol, both enantiomerically pure epoxides were converted to the corresponding olefins for cross metathesis. Subsequent transformations, including epoxide ring opening, esterifications, cyclopropanation, oxidation and ring-closing metathesis, provided the target molecule. This synthesis successfully addresses previous shortcomings in preparing brevipolides.

Graphical abstract: Enantioselective synthesis of (+)-brevipolide H

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Supplementary files

Article information


Submitted
17 May 2016
Accepted
13 Jun 2016
First published
14 Jun 2016

Org. Biomol. Chem., 2016,14, 6762-6768
Article type
Paper

Enantioselective synthesis of (+)-brevipolide H

C. Chen and D. Hou, Org. Biomol. Chem., 2016, 14, 6762
DOI: 10.1039/C6OB01071G

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