Abstract
An expedient and concise synthesis of (S)-trans-gamma-monocyclofamesol is here described. The aforementioned sesquiterpene was prepared starting from enantioenriched (S)-gamma-dihydroionone, which was in turn obtained from racemic alpha-ionone through the combined use of two previously developed processes. Key steps of the presented synthesis are the stereoselective Homer-Wadsworth-Emmons reaction between triethyl phosphonoacetate and gamma-dihydroionone and the effective fractional crystallization of the gamma-monocyclofamesol-3,5-dinitrobenzoate esters. By these means the target compound was obtained in good yield and with very high stereoisomeric purity.
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