title: Enantioselective synthesis of four isomers of 3-hydroxy-4-methyltetradecanoic acid, the constituent of antifungal cyclodepsipeptides W493 A and B.
abstract: Four possible stereoisomers of 3-hydroxy-4-methyltetradecanoic acid were enantioselectively synthesized by using Sharpless epoxidation and a subsequent epoxide-ring opening reaction with trimethylaluminum as the key steps. The absolute configuration of the beta-oxyacid component of antifungal cyclodepsipeptides W493 A and B was consequently determined as 3S,4R.
authors.affiliation: Department of Biochemistry and Biotechnology, Faculty of Agriculture and Life Science, Hirosaki University, Hirosaki, Japan.
authors.forename: Ken-ichi
authors.initials: K
authors.lastname: Nihei
authors.forename: Kimiko
authors.initials: K
authors.lastname: Hashimoto
authors.forename: Kazuo
authors.initials: K
authors.lastname: Miyairi
authors.forename: Toshikatsu
authors.initials: T
authors.lastname: Okuno
mesh_terms: D000935:Antifungal Agents / Q000737:chemistry*; D015394:Molecular Structure; D009227:Myristic Acids / Q000138:chemical synthesis*; D010456:Peptides, Cyclic / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: C500253:3-hydroxy-4-methyltetradecanoic acid; D000935:Antifungal Agents; D009227:Myristic Acids; D010456:Peptides, Cyclic; C500254:W493 A; C500255:W493 B