𝔖 Bobbio Scriptorium
✦   LIBER   ✦

Synthesis of methyl (5Z, 8Z, 11Z, 14Z, 17E)-eicosapentaenoate and methyl (4Z, 7Z, 10Z, 13Z, 16Z, 19E)-docosahexaenoate

✍ Scribed by Jean-Michel Vatèle; Huynh Dong Doan; Jean-Michel Chardigny; Jean-Louis Sébédio; André Grandgirard

Publisher
Elsevier Science
Year
1994
Tongue
English
Weight
708 KB
Volume
74
Category
Article
ISSN
0009-3084

No coin nor oath required. For personal study only.

✦ Synopsis

3Z,6Z,9Z,12E)-Pentadecatetraenal, a common intermediate in the synthesis of methyl A l7t EPA and methyl A I9t DHA, was obtained by copper(I)-catalyzed coupling between the Grignard reagent of I, 1-diethoxy-3-butyne and (Z, E)l-bromo-5,8-undecadien-2-yne followed by semi-hydrogenation of the resulting diendyne. The tetraenic aldehyde was subjected to a Wittig reaction with the ylide of (3-carboxybutyl)triphenylphosphonium bromide or of [6-(2,6,7trioxabicyclo [2.2.2] octyl)-hex-3-Z-enyl] triphenylphosphonium iodide to give, respectively AlTt EPA and the protected A19t DHA in high isomeric purity.

📜 SIMILAR VOLUMES

Synthesis of (9Z,12E)- and (9E,12Z)-[1-1
Synthesis of (9Z,12E)- and (9E,12Z)-[1-14C]linoleic acid and (5Z,8Z,11Z,14E)-[1-14C]arachidonic ácid
✍ Olivier Berdeaux; Jean-Michel Vatèle; Thierry Eynard; Mohammed Nour; Didier Poul 📂 Article 📅 1995 🏛 Elsevier Science 🌐 English ⚖ 741 KB

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