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

Maud Reiter, Staffan Torssell, Sandra Lee, David W.C. MacMillan

Research output: Contribution to journalArticlepeer-review

74 Scopus citations

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.

Original languageEnglish (US)
Pages (from-to)37-42
Number of pages6
JournalChemical Science
Volume1
Issue number1
DOIs
StatePublished - Jul 2010

All Science Journal Classification (ASJC) codes

  • Chemistry(all)

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