title: Stereoconvergent route to chiral cyclohexenone building blocks: formal synthesis of (-)-dysidiolide.
abstract: A stereoconvergent access to chiral carbocyclic building blocks is reported. 6-(3'-Hydroxy-4'-methylpent-4'-enyl)-3-methoxy cyclohex-2-enone () that consists of four stereoisomers, i.e., racemic ca. 1 : 1 diastereomers, is converted to enantiomerically pure carbocycles through a combination of regioselective catalytic asymmetric reduction and alkylative remote stereoinduction. The present stereoconvergent strategy has allowed the formal synthesis of bioactive (-)-dysidiolide.
authors.affiliation: Graduate School of Pharmaceutical Sciences, Osaka University, 1-6 Yamadaoka, Suita, Osaka 565-0871, Japan.
authors.forename: Gamal A I
authors.initials: GA
authors.lastname: Moustafa
authors.forename: Yasumasa
authors.initials: Y
authors.lastname: Kamada
authors.forename: Tetsuaki
authors.initials: T
authors.lastname: Tanaka
authors.forename: Takehiko
authors.initials: T
authors.lastname: Yoshimitsu
mesh_terms: D015107:4-Butyrolactone / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D053138:Cyclohexenes / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D053138:Cyclohexenes; C121906:dysidiolide; D015107:4-Butyrolactone