Asymmetric total synthesis of (+)-hexachlorosulfolipid, a cytotoxin isolated from Adriatic mussels.
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.
Yoshimitsu
Takehiko
T
Graduate School of Pharmaceutical Sciences, Osaka University, 1-6 Yamadaoka, Suita, Osaka 565-0871, Japan. yoshimit@phs.osaka-u.ac.jp
Fukumoto
Naoya
N
Nakatani
Ryo
R
Kojima
Naoto
N
Tanaka
Tetsuaki
T
D000818:Animals; D003198:Computer Simulation; D008055:Lipids / Q000138:chemical synthesis* / Q000737:chemistry / Q000302:isolation & purification; D008968:Molecular Conformation; D049878:Mytilus / Q000737:chemistry*; D013237:Stereoisomerism
D008055:Lipids; C553538:hexachlorosulfolipid