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The synthesis of d6-α-farnesene

✍ Scribed by Simon Fielder; Daryl D. Rowan

Publisher
John Wiley and Sons
Year
1994
Tongue
French
Weight
570 KB
Volume
34
Category
Article
ISSN
0022-2135

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✦ Synopsis

Abstract

D~6~‐α‐Farnesene (3,7‐dimethyl‐11‐^2^H~3~‐methyl‐12,12,12‐^2^H~3~‐dodeca‐1,3E,6E,10‐tetraene) has been synthesised by two routes. Thermolysis of 2‐geranyl‐3‐methylsulpholene (5) yielded unlabelled α‐farnesene (93%) which was epoxidized at Δ10 in 31% yield. Oxidative cleavage of the epoxide (42%) and Wittig elaboration of the resultant trienal with d~6~‐isopropyl triphenylphosphorane gave d~6~‐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.

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