Enzymatic resolution of (+/-)-epoxy-beta-cyclogeraniol, a synthetic precursor for abscisic acid analogs.
Lipase-catalyzed optical resolution of (+/-)-epoxy-beta-cyclogeraniol (1), a key synthetic intermediate for epoxy-beta-ionylideneacetic acid, was achieved in high enantiomeric purity. Transesterification with vinyl acetate by using lipase P (Nagase) made enriched (-)-1, while hydrolysis of the corresponding acetate by using lipase P (Amano) afforded (+)-1 with a high E value (E = 1600).
Okazaki
R
R
Division of Life Science, Graduate School of Agricultural Science, Tohoku University, Sendai, Japan.
Kiyota
H
H
Oritani
T
T
D000040:Abscisic Acid / Q000031:analogs & derivatives*; D000080462:Acyclic Monoterpenes; D007210:Indoleacetic Acids / Q000138:chemical synthesis*; D008049:Lipase; D008968:Molecular Conformation; D013729:Terpenes / Q000737:chemistry*
D000080462:Acyclic Monoterpenes; D007210:Indoleacetic Acids; D013729:Terpenes; D000040:Abscisic Acid; D008049:Lipase; C007836:geraniol