Journal
CHEMICAL SCIENCE
Volume 1, Issue 1, Pages 37-42Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c0sc00204f
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Funding
- NIHGMS [R01 01 GM093213-01]
- CIES
- Luxembourgish Ministry of Higher Education [BFR-05-131]
- NPSC
- NATIONAL INSTITUTE OF GENERAL MEDICAL SCIENCES [R01GM093213] Funding Source: NIH RePORTER
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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.
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