Journal of the American Chemical Society, Vol.119, No.1, 22-26, 1997
Synthesis of (-)-Haliclonadiamine
Diastereoselective and enantioselective hydrogenation of the racemic beta-keto ester 5 to give the enantiomerically pure (96% ee) ester 8 is reported. The conversion of the derived vinylstannane 11 to the antibiotic marine alkaloid (-)-haliclonadiamine (1) is describedl.
Keywords:BETA-KETO-ESTERS;CATALYZED ASYMMETRIC HYDROGENATION;DYNAMIC KINETIC RESOLUTION;3-OXO CARBOXYLIC ESTERS;FUNCTIONALIZED KETONES;HALICLONA SP;COMPLEXES;ELECTROPHILES;SPONGE;ACCESS