Related Experiment Video
Updated: May 14, 2026

Functionalized Spirocyclic Heterocycle Synthesis and Cytotoxicity Assay
Published on: February 9, 2021
A practical, enantiospecific synthesis of (S)-trans-gamma-monocyclofarnesol
1CNR, Istituto di Chimica del Riconoscimento Molecolare, Via Mancinelli, 71-20131 Milano, Italy. stefano.serra@cnr.it
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.
Related Concept Videos
Alkylation of β-Diester Enolates: Malonic Ester Synthesis
Synthesis of α-Substituted Carbonyl Compounds: The Stork Enamine Reaction
Diels–Alder Reaction Forming Cyclic Products: Stereochemistry
Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide
Naming Enantiomers
Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation

