Synthesis of (+)- and (–)-homononactic acid from (S)-1,2-epoxybutane. Total synthesis of tetranactin by ‘reverse coupe du roi’

Abstract

The synthesis of (+)- and (–)-homononactic acid was achieved in 6 steps and 4 steps respectively starting with the reaction of 2-lithium-5-vinylfuran and (S)-(–)-1,2-epoxybutane; both enantiomers were used in the construction of the achiral macrolide antibiotic tetranactin by esterification and subsequent lactonisation with the thiolester of 3-cyano-4,6-dimethyl-2-thiopyridone.