title: Stereoselective synthesis of a promising flower-inducing KODA analog, (9R,12S,13R,15Z)-9-hydroxy-12,13-methylene-10-oxooctadec-15-enoic acid.
abstract: Stereoselective synthesis of a promising flower-inducing 9,10-ketol octadecadienoic acid (KODA) analog, (9R,12S,13R,15Z)-9-hydroxy-12,13-methylene-10-oxooctadec-15-enoic acid, was designed to obtain the desired stereoisomer via coupling between chiral sulfone and aldehyde segments. A known chiral cyclopropane derivative was converted to the sulfone segment via carbon-chain elongation and sulfonylation. Dec-9-en-1-ol was converted to the aldehyde segment, whose C-9 configuration was introduced by Sharpless asymmetric dihydroxylation. Coupling of the both segments and subsequent assembly gave the desired (9R,12S,13R,15Z)-analog. The (9S,12S,13R,15Z)-analog was also synthesized by using the enatiomeric aldehyde segment. This strategy made it possible to synthesize the remaining stereoisomeric analogs.
authors.affiliation: Department of Bioresource Science, College of Agriculture, Ibaraki University, Ibaraki, Japan.
authors.forename: Shin
authors.initials: S
authors.lastname: Shimomura
authors.forename: Shuho
authors.initials: S
authors.lastname: Oyama
authors.forename: Kyohei
authors.initials: K
authors.lastname: Nakano
authors.forename: Morifumi
authors.initials: M
authors.lastname: Hasegawa
authors.forename: Hiroaki
authors.initials: H
authors.lastname: Toshima
mesh_terms: D002851:Chromatography, High Pressure Liquid; D005231:Fatty Acids, Unsaturated / Q000138:chemical synthesis*; D035264:Flowers / Q000187:drug effects / Q000254:growth & development*; D019787:Linoleic Acid / Q000737:chemistry / Q000378:metabolism; D008697:Methane / Q000031:analogs & derivatives / Q000737:chemistry / Q000378:metabolism; D013237:Stereoisomerism
chemical_list: D005231:Fatty Acids, Unsaturated; C030011:carbene; C027369:octadecadienoic acid; D019787:Linoleic Acid; D008697:Methane