Synthesis of (9Z,12E)- and (9E,12Z)-[1-14C]linoleic acid and (5Z,8Z,11Z,14E)-[1-14C]arachidonic ácid

✍ Scribed by Olivier Berdeaux; Jean-Michel Vatèle; Thierry Eynard; Mohammed Nour; Didier Poullain; Jean-Pierre Noël; Jean-Louis Sébédio

• Publisher: Elsevier Science
• Year: 1995
• Tongue: English
• Weight: 741 KB
• Volume: 78
• Category: Article
• ISSN: 0009-3084
• DOI: 10.1016/0009-3084(95)02486-3

✦ Synopsis

3Z,6E)-l-Bromododeca-3,6-diene, a common intermediate in the synthesis of labelled 12t linoleic acid and 14t arachidonic acid, was obtained from (E)-3-nonyl-l-ol, in four steps, via conventional functional manipulations. Cross-coupling of this bromododecadiene with the Grignard reagent of l-chloro-5-(tetrahydropyranyloxy)pentane gave a C17 dienic ether which was further transformed in three steps to 12t-[1-14C]linoleic acid in 22% overall yield from 3-nonyl-l-ol (eight steps). The synthesis of 14t arachidonic acid involves a Wittig reaction between (Z)-7o(tbutyldiphenylsilyloxy)hept-3-enal and the ylide of (3Z,6E)-dodeca-3,6-dienyl-triphenylphosphonium bromide. The resulting C19 tetraenic ether was transformed in three steps to 14t [l-14C]arachidonic acid (isomeric and radiochemical purities > 99'7,). 9t Linoleic acid was obtained by a stepwise six-carbon elongation chain of both ends of (E)-6-(2-tetrahydropyranyloxy)-hex-3-enyltriphenylphosphonium salt in 20% overall yield.