Synthesis of methyl (5Z, 8Z, 11E, 14Z, 17Z)- and (5Z, 8Z, 11E, 14Z, 17E)-eicosapentaenoate (EPA Δ 11t and Δ11t, 17t)
✍ Scribed by Jean-Michel Vatèle; Huynh Dong Doan; Bernard Fenet; Jean-Michel Chardigny; Jean-Louis Sébédio
- Publisher
- Elsevier Science
- Year
- 1995
- Tongue
- English
- Weight
- 407 KB
- Volume
- 78
- Category
- Article
- ISSN
- 0009-3084
No coin nor oath required. For personal study only.
✦ Synopsis
Chemistry and Physics of LIPIDS Synthesis of methyl (5Z,8Z,11E,14Z,17Z)and (5Z,8Z,11E,14Z,17E)-eicosapentaenoate (EPA Allt and A1 lt,17t)
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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 resultin
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