title: Synthesis and antifungal activity of novel 14-membered benzomacrolides, as galbonolide analogues.
abstract: Asymmetric total synthesis of benzene analogues of galbonolide, a 14-membered antifungal macrolide, possessing a benzene ring instead of a conjugated diene structure, was achieved starting from chiral 1-aryl-1-propanol obtained by enzyme-catalyzed kinetic resolution with high enantioselectivity. Representatively, a method for the introduction of a methylthio and chloride function at the vinyl position was also established. The resulting analogues unfortunately exhibited very little antifungal potency in comparison with galbonolide A.
authors.affiliation: Banyu Tsukuba Research Institute, Banyu Pharmaceutical Co. Ltd., Okubo-3, Tsukuba, Ibaraki 300-2611, Japan. sakouhk@banyu.co.jp
authors.forename: Hiroki
authors.initials: H
authors.lastname: Sakoh
authors.forename: Shunji
authors.initials: S
authors.lastname: Sakuraba
authors.forename: Yuichi
authors.initials: Y
authors.lastname: Sugimoto
authors.forename: Hideaki
authors.initials: H
authors.lastname: Imamura
authors.forename: Hideki
authors.initials: H
authors.lastname: Jona
authors.forename: Koji
authors.initials: K
authors.lastname: Yamada
authors.forename: Rie
authors.initials: R
authors.lastname: Bamba-Nagano
authors.forename: Terutaka
authors.initials: T
authors.lastname: Hashizume
authors.forename: Hajime
authors.initials: H
authors.lastname: Morishima
mesh_terms: D000935:Antifungal Agents / Q000138:chemical synthesis* / Q000494:pharmacology*; D002384:Catalysis; D005658:Fungi / Q000187:drug effects; D007783:Lactones / Q000138:chemical synthesis* / Q000494:pharmacology*; D018942:Macrolides / Q000138:chemical synthesis* / Q000494:pharmacology*; D008826:Microbial Sensitivity Tests; D010084:Oxidation-Reduction; D013237:Stereoisomerism
chemical_list: D000935:Antifungal Agents; D007783:Lactones; D018942:Macrolides; C047784:rustmicin