Journal
ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 14, Issue 45, Pages 10667-10673Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c6ob02141g
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- JSPS KAKENHI [JP90153650]
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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.
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