THE SYNTHESIS OF D(6)-ALPHA-FARNESENE

Citation
S. Fielder et Dd. Rowan, THE SYNTHESIS OF D(6)-ALPHA-FARNESENE, Journal of labelled compounds & radiopharmaceuticals, 34(11), 1994, pp. 1075-1085
Citations number
24
Categorie Soggetti
Chemistry Analytical","Pharmacology & Pharmacy
ISSN journal
03624803
Volume
34
Issue
11
Year of publication
1994
Pages
1075 - 1085
Database
ISI
SICI code
0362-4803(1994)34:11<1075:TSOD>2.0.ZU;2-7
Abstract
d(6)-alpha-Famesene methyl-12,12,12-H-2(3)-dodeca-1,3E,6E,10-tetraene) has been synthesised by two routes. Thermolysis of 2-geranyl-3-methyl sulpholene (5) yielded unlabelled alpha-famesene (93%) which was epoxi dized at Delta 10 in 31% yield. Oxidative cleavage of the epoxide (42% ) and Wittig elaboration of the resultant trienal with d(6)-Isopropyl triphenylphosphorane gave d(6)-alpha-famesene (73%). Alternatively, se lective epoxidation of (5) gave the terminal 6',7' mono-epoxide in 74% yield. Oxidative cleavage (73%) and Wittig elaboration of the resulta nt aldehyde;yielded deuterated 2-geranyl-3-methylsulpholene (46%). The rmal elimination of sulphur dioxide afforded the title compound in 91% yield.