title: Syntheses of (±)-serratine, (±)-lycoposerramine T, and (±)-lycopoclavamine B.
abstract: The first total syntheses of (±)-serratine, (±)-lycoposerramine T, and (±)-lycopoclavamine B have been accomplished. The functionalized octahydroindane skeleton of these natural products was constructed by an efficient Diels-Alder reaction of an α-alkynylcyclopentenone and the stereoselective introduction of a tertiary hydroxyl group. Two of these natural products were divergently synthesized from the same synthetic intermediate at a later stage.
authors.affiliation: School of Pharmaceutical Sciences, Institute of Medical, Pharmaceutical and Health Sciences, Kanazawa University, Kakuma-machi, Kanazawa 920-1192, Japan.
authors.forename: Hisaaki
authors.initials: H
authors.lastname: Zaimoku
authors.forename: Hiroshi
authors.initials: H
authors.lastname: Nishide
authors.forename: Asami
authors.initials: A
authors.lastname: Nishibata
authors.forename: Naoya
authors.initials: N
authors.lastname: Goto
authors.forename: Tsuyoshi
authors.initials: T
authors.lastname: Taniguchi
authors.forename: Hiroyuki
authors.initials: H
authors.lastname: Ishibashi
mesh_terms: D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry; D003500:Cyclization; D061565:Cycloaddition Reaction; D007189:Indans / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D014315:Triterpenes / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D001688:Biological Products; D007189:Indans; D014315:Triterpenes; C583646:lycopoclavamine B; C583645:lycoposerramine T; C532698:serratin