✦ LIBER ✦

A convenient synthesis of 8- and 12-carbon deuterium-labelled aldehydic esters for use in the preparation of labelled fatty acids

✍ Scribed by R. O. Adlof

Publisher: John Wiley and Sons
Year: 1987
Tongue: French
Weight: 178 KB
Volume: 24
Category: Article
ISSN: 0022-2135
DOI: 10.1002/jlcr.2580240612

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✦ Synopsis

Methyl 8-oxooctanoate-4,5-d and methyl 12-oxododecanoate-4,5,8,9-d4 were prepared for use as inzermediates in the synthesis of a series of labelled fatty acid methyl esters. Synthesis of the two compounds began with monoozonization and sodium acetate cleavage of 1,4-cyclooctadiene and 1,5,9-~yclododecatriene, respectively. The resultant unsaturated aldehydic acids were converted to the acetal esters. The acetal esters were deuterated with Wilkinson's catalyst and hydrolyzed to the deuterium-labelled aldehydic esters. Overall yields were 47% and 49% and isotopic purities 97% and 89%, respectively.

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