Stereoselective synthesis of moenocinol and assignment of its carbon-13 nuclear magnetic resonance spectrum

RM Coates, MW Johnson

Index: Coates, Robert M.; Johnson, Mark W. Journal of Organic Chemistry, 1980 , vol. 45, # 13 p. 2685 - 2697

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Citation Number: 44

Abstract

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- ...