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A synthon for C‐20 trideuterated eicosanoids: Preparation of [ 2 H 3 ]‐arachidonic acid
Author(s) -
Prakash Chandra,
Saleh Samir,
Sweetman Brian J.,
Taber Douglass F.,
Blair Ian A.
Publication year - 1989
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.2580270507
Subject(s) - synthon , chemistry , wittig reaction , reagent , bromide , chemical synthesis , arachidonic acid , deuterium , organic chemistry , stereochemistry , in vitro , biochemistry , enzyme , physics , quantum mechanics
Starting from hex‐5‐yn‐1‐ol an efficient seven step synthesis of (Z)9‐[ 2 H 3 ](non‐3‐en‐1‐yl) triphenylphosphonium bromide is described. This Wittig reagent is a key intermediate for the synthesis of C‐20 trideuterated eicosanoids. Introduction of deuterium at C‐20 provides standards that are stable to a wide range of reagents and reaction conditions. The utility of the Wittig synthon was demonstrated by the preparation of C‐20 trideuterated arachidonic acid.