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
Externally publishedYes

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Cytotoxins
Chlorinated Hydrocarbons
Epoxy Compounds
Lipids
hexachlorosulfolipid

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Asymmetric total synthesis of (+)-Hexachlorosulfolipid, a cytotoxin isolated from adriatic mussels. / Yoshimitsu, Takehiko; Fukumoto, Naoya; Nakatani, Ryo; Kojima, Naoto; Tanaka, Tetsuaki.

In: Journal of Organic Chemistry, Vol. 75, No. 16, 20.08.2010, p. 5425-5437.

Research output: Contribution to journalArticle

Yoshimitsu, Takehiko ; Fukumoto, Naoya ; Nakatani, Ryo ; Kojima, Naoto ; Tanaka, Tetsuaki. / Asymmetric total synthesis of (+)-Hexachlorosulfolipid, a cytotoxin isolated from adriatic mussels. In: Journal of Organic Chemistry. 2010 ; Vol. 75, No. 16. pp. 5425-5437.
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