Stereoselective synthesis of (all-Z)-hentriaconta-3,6,9,12,15,19,22,25,28-nonaene
| Autor: | Martin Kirkhus Dahl, Ida Aarum, Yngve Stenstrøm, Liudmila Filippova, Trond Vidar Hansen, Martine Ringdal |
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| Rok vydání: | 2015 |
| Předmět: |
Magnetic Resonance Spectroscopy
Double bond Molecular Conformation Stereoisomerism Biochemistry chemistry.chemical_compound Organic chemistry Physical and Theoretical Chemistry chemistry.chemical_classification Aldehydes Biological Products Natural product Organic Chemistry Total synthesis Esters Lipid Metabolism Eicosapentaenoic acid Hydrocarbons Eicosapentaenoic Acid chemistry Drug Design Yield (chemistry) Wittig reaction Fatty Acids Unsaturated Stereoselectivity |
| Zdroj: | Organic & Biomolecular Chemistry. 13:4680-4685 |
| ISSN: | 1477-0539 1477-0520 |
| DOI: | 10.1039/c5ob00313j |
| Popis: | Several microorganisms produce small quantities of polyunsaturated hydrocarbons and such natural products are of interest. Starting from the ethyl ester of eicosapentaenoic acid, the total synthesis of the natural product (all-Z)-hentriaconta-3,6,9,12,15,19,22,25,28-nonaene has been achieved in eight steps and 15% overall yield. The synthesis is based on a stereoselective Wittig reaction and confirms the all-Z-configuration of the nine double bonds in this highly unsaturated natural product. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
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