title: A concise stereoselective synthesis of (-)-erycibelline.
abstract: (-)-Erycibelline, the dihydroxynortropane alkaloid isolated from Erycibe elliptilimba Merr. et Chun., was synthesized using a cyclic nitrone as advanced intermediate, wherein the key step was the SmI(2)-induced intramolecular reductive coupling of cyclic nitrone with aldehyde which resulted in good yield and stereoselectivity.
authors.affiliation: Beijing National Laboratory for Molecular Science (BNLMS), Institute of Chemistry, Chinese Academy of Sciences, Beijing 100191, China.
authors.forename: Zhao-Lan
authors.initials: ZL
authors.lastname: Zhang
authors.forename: Shinpei
authors.initials: S
authors.lastname: Nakagawa
authors.forename: Atsushi
authors.initials: A
authors.lastname: Kato
authors.forename: Yue-Mei
authors.initials: YM
authors.lastname: Jia
authors.forename: Xiang-Guo
authors.initials: XG
authors.lastname: Hu
authors.forename: Chu-Yi
authors.initials: CY
authors.lastname: Yu
mesh_terms: D000470:Alkaloids / Q000032:analysis / Q000138:chemical synthesis* / Q000494:pharmacology; D000818:Animals; D002626:Chemistry, Pharmaceutical / Q000379:methods*; D027722:Convolvulaceae / Q000737:chemistry; D003500:Cyclization; D006026:Glycoside Hydrolases / Q000037:antagonists & inhibitors* / Q000378:metabolism; D006801:Humans; D020128:Inhibitory Concentration 50; D009589:Nitrogen Oxides / Q000737:chemistry; D009662:Nortropanes / Q000032:analysis / Q000138:chemical synthesis* / Q000494:pharmacology; D010946:Plants, Medicinal / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000470:Alkaloids; D009589:Nitrogen Oxides; D009662:Nortropanes; C015388:nitrones; C052654:erycibelline; D006026:Glycoside Hydrolases