title: A practical, enantiospecific synthesis of (S)-trans-gamma-monocyclofarnesol.
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.
authors: CNR, Istituto di Chimica del Riconoscimento Molecolare, Via Mancinelli, 71-20131 Milano, Italy. stefano.serra@cnr.it
authors: Stefano
authors: S
authors: Serra
mesh_terms: D002855:Chromatography, Thin Layer; D003460:Crystallization; D008401:Gas Chromatography-Mass Spectrometry; D006863:Hydrogen-Ion Concentration; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D045792:Norisoprenoids / Q000737:chemistry; D012717:Sesquiterpenes / Q000138:chemical synthesis*; D013237:Stereoisomerism
chemical_list: C578736:(S)-trans-gamma-monocyclofarnesol; D007202:Indicators and Reagents; D045792:Norisoprenoids; D012717:Sesquiterpenes