New method for synthesizing the intermediates to 5-HETE from yeast-mediated reduction products by employing Baeyer-Villiger oxidation with complete retention of enantiomeric excess.
(R) and (S)-Aldehydes 2, which are intermediates for the synthesis of (5R) and (5S)-HETE, were respectively synthesized from the yeast-mediated reductive products, hydroxy ester 3 and cis-lactone 4, through Baeyer-Villiger oxidation with complete retention of enantiomeric excess.
Yamauchi
Satoshi
S
Faculty of Agriculture, Ehime University, Matsuyama, Japan. syamauch@agr.ehime-u.ac.jp
Kinoshita
Yoshihiro
Y
Kinoshita
Yoshiro
Y
D000447:Aldehydes / Q000737:chemistry / Q000378:metabolism; D001711:Biotransformation; D003517:Cyclopentanes / Q000737:chemistry / Q000378:metabolism; D004952:Esters / Q000737:chemistry / Q000378:metabolism; D006018:Glycols / Q000737:chemistry / Q000378:metabolism; D006893:Hydroxyeicosatetraenoic Acids / Q000096:biosynthesis / Q000138:chemical synthesis*; D006900:Hydroxylation; D007659:Ketones / Q000737:chemistry / Q000378:metabolism; D007783:Lactones / Q000737:chemistry / Q000378:metabolism; D010084:Oxidation-Reduction; D013237:Stereoisomerism; D015003:Yeasts / Q000378:metabolism*
D000447:Aldehydes; D003517:Cyclopentanes; D004952:Esters; D006018:Glycols; D006893:Hydroxyeicosatetraenoic Acids; D007659:Ketones; D007783:Lactones; C007201:cyclopentanone