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Synthesis of (2,3-13C2) erucic acid

✍ Scribed by Julie A. Olsen; Pablo A. Bukata

Publisher
John Wiley and Sons
Year
1993
Tongue
French
Weight
335 KB
Volume
33
Category
Article
ISSN
0022-2135

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✦ Synopsis

Abstract

The synthesis of (2,3‐^13^C~2~) erucic acid, for use in metabolic studies, is reported. The synthesis employs a repeated 3 step reaction sequence using ^13^C labeled triethylphosphonoacetate to extend C~18:1~, oleyl alcohol, by 4 carbons. The starting alcohol is first oxidized with PCC and the resulting aldehyde is condensed with triethyl(1‐^13^C)phosphonoacetate. The product, an α,β unsaturated ester, is reduced with (Ph~3~PCuH)~6~ to ethyl eicosenoate. Reduction with LAH gives eicosenoyl alcohol. A repetition of the reaction sequence using triethyl(2‐^13^C) phosphonoacetate results in ethyl(2,3‐^13^C~2~)erucate. The (2,3‐^13^C~2~) erucic acid, obtained by hydrolysis with alcoholic KOH, gave ^13^C NMR signals of δ 24.6 and 34.1 ppm for C‐3 and C‐2 respectively with a J=34.9 Hz. The overall yield was 5.5%.

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