In order to study the effect of the double bonds geometry of linolenic acid (18:3 n-3) on its biological activities, (gz,12Z, I 5E)-and (9E, I 2Z, 15Z)-octadecatrienoic acids, found in many refined vegetable oils, were made by total synthesis. Synthesis of 18:3 A9c, 12c, 1St involves a Wittig reacti
Synthesis of (6Z,9Z,11E)-octadecatrienoic and (8Z,11Z,13E)-eicosatrienoic acids and their [1-14C]-radiolabeled analogs
✍ Scribed by Silke Gnädig; Olivier Berdeaux; Olivier Loreau; Jean-Pierre Noël; Jean-Louis Sébédio
- Book ID
- 108313232
- Publisher
- Elsevier Science
- Year
- 2001
- Tongue
- English
- Weight
- 204 KB
- Volume
- 112
- Category
- Article
- ISSN
- 0009-3084
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## Abstract For studies into the relationship between their physical properties and chemical structure, several polyunsaturated fatty acids related to (__Z,Z,Z__)‐6,9,12‐octadecatrienoic acid and (__Z,Z,Z__)‐8,11,14‐eicosatrienoic acid were synthesized. Methyl (__E,Z,Z__)‐2,11,14‐eicosatrienoate a
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
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