Asymmetric total synthesis of (+)-Hexachlorosulfolipid, a cytotoxin isolated from adriatic mussels

Takehiko Yoshimitsu, Naoya Fukumoto, Ryo Nakatani, Naoto Kojima, Tetsuaki Tanaka

Research output: Contribution to journalArticle

45 Citations (Scopus)

Abstract

The enantioselective total synthesis of (+)-hexachlorosulfolipid, a cytotoxin found in the Adriatic mussel Mytilus galloprovincialis, is described. The unique chlorinated hydrocarbon motif of the lipid is successfully furnished by a series of dichlorination reactions of chiral epoxides with chlorophosphonium reagent generated in situ from Ph3P/NCS. The present total synthesis has allowed the confirmation of the absolute configuration of the natural cytotoxic (+)-hexachlorosulfolipid originally proposed by Fattorusso, Ciminiello, and co-workers.

Original languageEnglish
Pages (from-to)5425-5437
Number of pages13
JournalJournal of Organic Chemistry
Volume75
Issue number16
DOIs
Publication statusPublished - Aug 20 2010

ASJC Scopus subject areas

  • Organic Chemistry

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