Total synthesis of unsaturated trihydroxy C18 fatty acids
✍ Scribed by Benjamin Gossé-Kobo; Paul Mosset; René Grée
- Publisher
- Elsevier Science
- Year
- 1989
- Tongue
- French
- Weight
- 145 KB
- Volume
- 30
- Category
- Article
- ISSN
- 0040-4039
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✦ Synopsis
The total synthesis, in chiral form, of unsaturated trlhydroxy Clg fatty acids 13 and 14 as methyl esters, s&ting from natural tartaric acid via the key intermediate aldehyde 5 is reported.
Little is known about the biological importance of oxygenated fatty acids metabolitcs in vegetals.
Then, it is interesting to point out that Kato and coworkers isolated from rice plants several oxygenated Cl8 fatty acids which can act as self-defense substances against rice blast disease (1). Among these were the triols 1 to 4.
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This article reviews synthetic routes leading to polyunsaturated fatty acids having "skipped" double bonds. Emphasis is placed on the "acetylenic approach". The suitability of building blocks, their condensation reactions as well as the controlled reduction of triple bonds to cis double bonds are d
Structural elucidation including the absolute configuration was carried out on the trihydroxy Cl8 -fatty acids isolated from rice plant, Sasanishiki suffered from rice blast disease.
The synthesis of all isomeric Cta furan-containiaag fatty acids from furan, furfura~ or methyl octadc~ynoate is described. ## A. 2,5-Epoxyoctadeca-2,4-dienoic acid (1) 1. 2.Trldec-l '-enylfuran A mixture of 1.bromododecane (43.7 g, 3.t75 reel), triphenylphosphine (46 g,