The synthesis of d6-α-Farnesene

Article abstract of DOI:10.1002/jlcr.2580341111

d₆-α-Farnesene (3,7-dimethyl-11-²H₃-methyl-12,12,12-²H₃-dodeca-1,3E,6E,10 -tetraene) has been synthesised by two routes. Thermolysis of 2-geranyl-3-methylsulpholene (5) yielded unlabelled α-famesene (93%) which was epoxidized at Δ10 in 31% yield. Oxidative cleavage of the epoxide (42%) and Wittig elaboration of the resultant trienal with d₆-isopropyl triphenylphosphorane gave d₆-α-farnesene (73%). Alternatively, selective epoxidation of (5) gave the terminal 6',7' mono-epoxide in 74% yield. Oxidative cleavage (73%) and Wittig elaboration of the resultant aldehyde yielded deuterated 2-geranyl-3-methylsulpholene (46%). Thermal elimination of sulphur dioxide afforded the title compound in 91% yield.