Enantioselective synthesis of four isomers of 3-hydroxy-4-methyltetradecanoic acid, the constituent of antifungal cyclodepsipeptides W493 A and B.
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.
Nihei
Ken-ichi
K
Department of Biochemistry and Biotechnology, Faculty of Agriculture and Life Science, Hirosaki University, Hirosaki, Japan.
Hashimoto
Kimiko
K
Miyairi
Kazuo
K
Okuno
Toshikatsu
T
D000935:Antifungal Agents / Q000737:chemistry*; D015394:Molecular Structure; D009227:Myristic Acids / Q000138:chemical synthesis*; D010456:Peptides, Cyclic / Q000737:chemistry*; D013237:Stereoisomerism
C500253:3-hydroxy-4-methyltetradecanoic acid; D000935:Antifungal Agents; D009227:Myristic Acids; D010456:Peptides, Cyclic; C500254:W493 A; C500255:W493 B