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Synthesis of [8,9,10,11‐ 13 C 4 ]leukotriene C 4
Author(s) -
Raftery Mark J.,
Gaskell Simon J.
Publication year - 1991
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.2580290309
Subject(s) - wittig reaction , chemistry , triphenylphosphine , dichloromethane , triethylamine , medicinal chemistry , hydride , organic chemistry , catalysis , hydrogen , solvent
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 .