title: Biomimetic conversion of (3S)-(-)-neodictyoprolenol to optically pure (1S,2R)-(-)-dictyopterene B, marine algal sex pheromone.
abstract: 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.
authors.affiliation: Department of Biological Chemistry, Faculty of Agriculture, Yamaguchi University, Yamaguchi 753-8515, Japan. kajiwara@agr.yamaguchi-u.ac.jp
authors.forename: Tadahiko
authors.initials: T
authors.lastname: Kajiwara
authors.forename: Yuuko
authors.initials: Y
authors.lastname: Yamamoto
authors.forename: Yoshihiko
authors.initials: Y
authors.lastname: Akakabe
authors.forename: Kenji
authors.initials: K
authors.lastname: Matsui
authors.forename: Hiroshi
authors.initials: H
authors.lastname: Shimizu
authors.forename: Tesuo
authors.initials: T
authors.lastname: Kawai
mesh_terms: 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
chemical_list: D005233:Fatty Alcohols; D007202:Indicators and Reagents; D012724:Sex Attractants; C426843:neodictyoprolenol