title: Total Synthesis of Resolvin D5.
abstract: Resolvin D5 (RvD5) is a metabolite of docosahexanoic acid with anti-inflammatory activity that has not yet been thoroughly investigated because of its low biological availability. A synthetic route to optically active RvD5 was developed by assembling the C1-C10 aldehyde, C11-C13 phosphonium salt, and C14-C22 aldehyde building blocks. The aldehyde fragments were prepared by Sharpless asymmetric epoxidation of corresponding racemic (E)-1-TMS-1-alken-3-ols followed by reaction of the TBS ethers of the resulting epoxy alcohols with Et2AlCN and DIBAL reduction of the (E)-1-cyano-1-alken-3-ol derivatives. The C14-C22 aldehyde was connected with the C11-C13 fragment, i.e., [TBSO(CH2)3PPh3]+Br-, by Wittig reaction. The resulting C11-C22 intermediate was converted to the phosphonium salt, which was attached to the C1-C10 aldehyde by Wittig reaction to yield the structure of RvD5.
authors.affiliation: Department of Biotechnology, Tokyo Institute of Technology , B-52, Nagatsuta-cho 4259, Midori-ku, Yokohama 226-8501, Japan.
authors.forename: Narihito
authors.initials: N
authors.lastname: Ogawa
authors.affiliation: Department of Biotechnology, Tokyo Institute of Technology , B-52, Nagatsuta-cho 4259, Midori-ku, Yokohama 226-8501, Japan.
authors.forename: Takuo
authors.initials: T
authors.lastname: Sugiyama
authors.affiliation: Department of Biotechnology, Tokyo Institute of Technology , B-52, Nagatsuta-cho 4259, Midori-ku, Yokohama 226-8501, Japan.
authors.forename: Masao
authors.initials: M
authors.lastname: Morita
authors.affiliation: Department of Biotechnology, Tokyo Institute of Technology , B-52, Nagatsuta-cho 4259, Midori-ku, Yokohama 226-8501, Japan.
authors.forename: Yuta
authors.initials: Y
authors.lastname: Suganuma
authors.affiliation: Department of Biotechnology, Tokyo Institute of Technology , B-52, Nagatsuta-cho 4259, Midori-ku, Yokohama 226-8501, Japan.
authors.forename: Yuichi
authors.identifier: 0000-0002-4385-9531
authors.initials: Y
authors.lastname: Kobayashi
mesh_terms: D004281:Docosahexaenoic Acids / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure
chemical_list: C572765:resolvin D5; D004281:Docosahexaenoic Acids