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Synthesis of d8-geranyl diphosphate

✍ Scribed by Daniel J. Comeskey; Daryl D. Rowan; Adam J. Matich

Publisher
John Wiley and Sons
Year
2006
Tongue
French
Weight
122 KB
Volume
49
Category
Article
ISSN
0022-2135

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✦ Synopsis

Multiply labelled d 8 -geranyl diphosphate (3-methyl-7-2 H 3 -methyl-[1,1,8,8,8]-2 H 5 -2E,6-octadienyl diphosphate) was synthesised from geraniol in 8 steps. Geraniol was converted to [1,1]-2 H 2 -geraniol by a three step oxidation-reduction sequence in 38% yield. Selective epoxidation of [1,1]-2 H 2 -geranyl acetate gave 6,7-epoxy-[1,1]-2 H 2geranyl 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.

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