1. Asymmetric Total Synthesis of (+)-Hexachlorosulfolipid, a Cytotoxin Isolated from Adriatic Mussels
- Author
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Tetsuaki Tanaka, Naoto Kojima, Ryo Nakatani, Naoya Fukumoto, and Takehiko Yoshimitsu
- Subjects
Mytilus ,In situ ,animal structures ,biology ,Chemistry ,Stereochemistry ,fungi ,Organic Chemistry ,Molecular Conformation ,Enantioselective synthesis ,Absolute configuration ,Total synthesis ,Epoxide ,Stereoisomerism ,Mussel ,biology.organism_classification ,Lipids ,chemistry.chemical_compound ,Reagent ,Animals ,Computer Simulation - 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 Ph(3)P/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.
- Published
- 2010
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