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Asymmetric synthesis of 12-hydroxyheptadecatrienoic acid and its 5,6-dihydro- and 14,15-dehydro-derivatives.
- Source :
-
Organic & biomolecular chemistry [Org Biomol Chem] 2016 Dec 07; Vol. 14 (45), pp. 10667-10673. Date of Electronic Publication: 2016 Oct 27. - Publication Year :
- 2016
-
Abstract
- Natural 12-hydroxyheptadecatrienoic acid (12-HHT) with an S configuration was synthesised by a Suzuki-Miyaura coupling of C10-C17 iodo alcohol with C1-C9 vinylborane. The iodo alcohol was synthesised by utilising Sharpless asymmetric epoxidation of the corresponding trimethylsilyl alcohol. The method yielded more than 100 mg of 12-HHT. Similarly, syntheses of 5,6-dihydro- and 14,15-dehydro derivatives of 12-HHT, known as HHD and HHTE, respectively, were completed in a stereoselective manner.
- Subjects :
- Alcohols chemical synthesis
Alcohols chemistry
Boranes chemical synthesis
Boranes chemistry
Epoxy Compounds chemical synthesis
Epoxy Compounds chemistry
Fatty Acids, Unsaturated chemistry
Stereoisomerism
Vinyl Compounds chemical synthesis
Vinyl Compounds chemistry
Fatty Acids, Unsaturated chemical synthesis
Subjects
Details
- Language :
- English
- ISSN :
- 1477-0539
- Volume :
- 14
- Issue :
- 45
- Database :
- MEDLINE
- Journal :
- Organic & biomolecular chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 27786324
- Full Text :
- https://doi.org/10.1039/c6ob02141g