Premium
Synthesis of d 8 ‐geranyl diphosphate
Author(s) -
Comeskey Daniel J.,
Rowan Daryl D.,
Matich Adam J.
Publication year - 2006
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/jlcr.1027
Subject(s) - geraniol , chemistry , geranyl acetate , yield (engineering) , epoxide , wittig reaction , stereochemistry , organic chemistry , catalysis , chromatography , materials science , essential oil , metallurgy
Multiply labelled d 8 ‐geranyl diphosphate (3‐methyl‐7‐ 2 H 3 ‐methyl‐[1,1,8,8,8]‐ 2 H 5 ‐2 E ,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 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 © 2005 John Wiley & Sons, Ltd.
Accelerating Research
Robert Robinson Avenue,
Oxford Science Park, Oxford
OX4 4GP, United Kingdom
Address
John Eccles HouseRobert Robinson Avenue,
Oxford Science Park, Oxford
OX4 4GP, United Kingdom