A stereoselective synthesis of moenocinol (l), the sesterterpene alcohol liberated by hydrolysis of the antibiotic moenomycin, is described. Alkylation of isobutyric acid dianion with 5-bromo-1-pentene followed by reduction with lithium aluminum hydride and benzylation provided l-(benzyloxy)-2, 2-dimethyl-6-heptene(4). Hydrolysis and cleavage of the epoxide of 4 with periodic acid gave 6-(benzyloxy)-5, 5-dimethylhexanal(6). 2-(Phenyl- ...
