Synthesis of d8-geranyl diphosphate

Multiply labelled d(8)-geranyl diphosphate (3-methyl-7-H-2(3)-methyl-[1,1,8,8,8]-H-2(5)-2E,6-octadienyl diphosphate) was synthesised from geraniol in 8 steps. Geraniol was converted to [1,1]-H-2(2)-geraniol by a three step oxidation-reduction sequence in 38% yield. Selective epoxidation of [1,1]-H-2(2)-geranyl acetate gave 6,7-epoxy-[1,1]-H-2(2)-geranyl acetate, which, on oxidative cleavage of the epoxide and Wittig elaboration with d(6)-isopropyl triphenylphosphorane, gave d(8)-geraniol (14% yield) which was, in turn, converted to the title compound. Copyright (c) 2005 John Wiley & Sons, Ltd.