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Synthesis of 7,10-dihydroxy-8(E)-octadecenoic acid
| Content Provider | Semantic Scholar |
|---|---|
| Author | Mhaskar, Sudhakar Yeshwant Subbarao, Raghav |
| Copyright Year | 1993 |
| Abstract | We report the synthesis of 7,10-dihydroxy-8(E)-octadecenoic acid (DOD), which has recently also been reported from bioconversion of oleic acid. One hydroxyl of 1,7-heptanediol was protected as tetrahydropyranyl ether, and the other hydroxyl was used for chain extension by two carbonsvia Wittig reaction to give ethyl 9-tetrahydropyranyloxy-2(E)-nonenoate, an α,β-unsaturated ester, which on Dibal-H reduction offered allylic alcohol. The epoxidation at the double bond followed by conversion of the hydroxyl group to chloro gave 9-tetrahydropyranyloxy-2,3-oxirane-1-chlorononane. Treatment of this epoxy nonyl chloride with excess of LiNH2/liquid NH3; followed by addition of 1-nonanal, gave 18-tetrahydropyranyloxy-9, 12-dihydroxy-10-octadecyne. The lithium aluminum hydride reduction of the conjugated hydroxy acetylenic bond, protection of hydroxyl groups as benzoates and oxidation of the primary ether group, followed by removal of benzoate groups, gave DOD. |
| Starting Page | 519 |
| Ending Page | 522 |
| Page Count | 4 |
| File Format | PDF HTM / HTML |
| DOI | 10.1007/BF02542587 |
| Volume Number | 70 |
| Alternate Webpage(s) | https://page-one.springer.com/pdf/preview/10.1007/BF02542587 |
| Alternate Webpage(s) | https://doi.org/10.1007/BF02542587 |
| Language | English |
| Access Restriction | Open |
| Content Type | Text |
| Resource Type | Article |
