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Synthesis of [8,9,10,11-13C4]leukotriene C4

✍ Scribed by Mark J. Raftery; Simon J. Gaskell

Publisher
John Wiley and Sons
Year
1991
Tongue
French
Weight
273 KB
Volume
29
Category
Article
ISSN
0022-2135

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✦ Synopsis

Abstract

A “one pot” reduction of ethyl [1,2‐^13^C~2~]bromoacetate with diisobutylaluminium hydride in dichloromethane, followed by reaction with triphenylphosphine, then triethylamine, yields [1,2‐^13^C~2~]formylmethylenetriphenylphosphorane. Consecutive Wittig reactions of [1,2‐^13^C~2~] formylmethylenetriphenylphosphorane with methyl 5(S),6(R)‐epoxy‐6‐formylhexanoate and subsequent Wittig reaction with Z‐3‐nonen‐ 1‐triphenylphosphorane yields [8,9,10,11‐^13^C~4~]LTA~4~ methyl ester, which is readily converted to [8,9,10,11‐^13^C~4~]LTC~4~.

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