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Chem Sci. 2010 Jul;1(1):37-42.

The organocatalytic three-step total synthesis of (+)-frondosin B.

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  • 1Merck Center for Catalysis at Princeton University, Princeton, New Jersey, 08544, USA.

Abstract

The frondosins are a family of marine sesquiterpenes isolated from the sponge Dysidea frondosa that exhibit biological activities ranging from anti-inflammatory properties to potential application in anticancer and HIV therapy. Herein, a concise enantioselective total synthesis of (+)-frondosin B is described which requires a total of three chemical steps. The enantioselective conjugate addition of a benzofuran-derived boronic acid to crotonaldehyde in the presence of an imidazolidinone organocatalyst builds the critical stereogenic center of frondosin B in the first operation, while the remaining two ring systems of this natural product are installed in the two subsequent steps. A combination of X-ray crystallographic data, deuterium labeling, and chemical correlation studies provides further evidence as to the correct absolute stereochemical assignment of (+)-frondosin B.

PMID:
22299067
[PubMed]
PMCID:
PMC3268339
Free PMC Article

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