Stereoselective total synthesis of a potent natural antifungal compound (6S)-5,6,dihydro-6-[(2R)-2-hydroxy-6-phenyl hexyl]-2H-pyran-2-one.
A practical stereoselective synthesis of (6S)-5,6,dihydro-6-[(2R)-2-hydroxy-6-phenyl hexyl]-2H-pyran-2-one, a potent natural antifungal compound, is described. The sequence involves diastereoselective iodine-induced electrophilic cyclization, epoxide ring opening with a vinyl Grignard reagent and ring closing metathesis (RCM) as the key steps.
Das
Biswanath
B
Organic Chemistry Division-I, Indian Institute of Chemical Technology, Hyderabad 500 007, India. biswanathdas@yahoo.com
Laxminarayana
Keetha
K
Krishnaiah
Martha
M
Kumar
Duddukuri Nandan
DN
D000935:Antifungal Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D002177:Candidiasis / Q000188:drug therapy; D002384:Catalysis; D003500:Cyclization; D015195:Drug Design; D004852:Epoxy Compounds / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D007700:Kinetics; D015394:Molecular Structure; D013237:Stereoisomerism; D013329:Structure-Activity Relationship; D050257:Tubulin Modulators / Q000138:chemical synthesis / Q000737:chemistry
D000935:Antifungal Agents; D004852:Epoxy Compounds; D050257:Tubulin Modulators