Biomimetic conversion of (3S)-(-)-neodictyoprolenol to optically pure (1S,2R)-(-)-dictyopterene B, marine algal sex pheromone.
Both enantiomers of (3S)-(-)- and (3R)-(+)-Neodictyoprolenol [(3S,5Z,8Z)-(-)-1,5,8-undecatrien-3-ol] were successfully converted to the algal sex pheromone, (1S,2R)-(-)-dictyopterene B and (1R,2S)-(+)-dictyopterene B in high enantiomeric purities (e. e. > 99%), respectively, by the biomimetic reaction involving phosphorylation and elimination under a mild condition.
Kajiwara
Tadahiko
T
Department of Biological Chemistry, Faculty of Agriculture, Yamaguchi University, Yamaguchi 753-8515, Japan. kajiwara@agr.yamaguchi-u.ac.jp
Yamamoto
Yuuko
Y
Akakabe
Yoshihiko
Y
Matsui
Kenji
K
Shimizu
Hiroshi
H
Kawai
Tesuo
T
D005233:Fatty Alcohols / Q000138:chemical synthesis / Q000737:chemistry* / Q000302:isolation & purification; D007202:Indicators and Reagents; D007564:Japan; D000459:Phaeophyceae / Q000737:chemistry*; D012724:Sex Attractants / Q000138:chemical synthesis / Q000737:chemistry* / Q000302:isolation & purification; D013237:Stereoisomerism
D005233:Fatty Alcohols; D007202:Indicators and Reagents; D012724:Sex Attractants; C426843:neodictyoprolenol