title: Asymmetric synthesis of 12-hydroxyheptadecatrienoic acid and its 5,6-dihydro- and 14,15-dehydro-derivatives.
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.
authors: School of Life Science and Technology, Tokyo Institute of Technology, Nagatsuta-cho 4259, Midori-ku, Yokohama 226-8501, Japan. ykobayas@bio.titech.ac.jp.
authors: Yuichi
authors: Y
authors: Kobayashi
authors: Masao
authors: M
authors: Morita
authors: Narihito
authors: N
authors: Ogawa
authors: Daiki
authors: D
authors: Kondo
authors: Toshifumi
authors: T
authors: Tojo
mesh_terms: D000438:Alcohols / Q000138:chemical synthesis / Q000737:chemistry; D001880:Boranes / Q000138:chemical synthesis / Q000737:chemistry; D004852:Epoxy Compounds / Q000138:chemical synthesis / Q000737:chemistry; D005231:Fatty Acids, Unsaturated / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D014753:Vinyl Compounds / Q000138:chemical synthesis / Q000737:chemistry
chemical_list: D000438:Alcohols; D001880:Boranes; D004852:Epoxy Compounds; D005231:Fatty Acids, Unsaturated; D014753:Vinyl Compounds; C008033:12-hydroxy-5,8,10-heptadecatrienoic acid