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Issue 1, 2010
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The organocatalytic three-step total synthesis of (+)-frondosin B

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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.

Graphical abstract: The organocatalytic three-step total synthesis of (+)-frondosin B

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Article information


Submitted
01 Mar 2010
Accepted
24 Mar 2010
First published
21 May 2010

Chem. Sci., 2010,1, 37-42
Article type
Edge Article

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

M. Reiter, S. Torssell, S. Lee and D. W. C. MacMillan, Chem. Sci., 2010, 1, 37
DOI: 10.1039/C0SC00204F

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