title: Syntheses of the Stemona alkaloids (+/-)-stenine, (+/-)-neostenine, and (+/-)-13-epineostenine using a stereodivergent Diels-Alder/azido-Schmidt reaction.
abstract: A tandem Diels-Alder/azido-Schmidt reaction sequence provides rapid access to the core skeleton shared by several Stemona alkaloids including stenine, neostenine, tuberostemonine, and neotuberostemonine. The discovery and evolution of inter- and intramolecular variations of this process and their applications to total syntheses of (+/-)-stenine and (+/-)-neostenine are described. The stereochemical outcome of the reaction depends on both substrate type and reaction conditions, enabling the preparation of both (+/-)-stenine and (+/-)-neostenine from the same diene/dienophile combination.
authors.affiliation: Department of Medicinal Chemistry, University of Kansas, Lawrence, Kansas 66045-7582, USA.
authors.forename: Kevin J
authors.initials: KJ
authors.lastname: Frankowski
authors.forename: Jennifer E
authors.initials: JE
authors.lastname: Golden
authors.forename: Yibin
authors.initials: Y
authors.lastname: Zeng
authors.forename: Yao
authors.initials: Y
authors.lastname: Lei
authors.forename: Jeffrey
authors.initials: J
authors.lastname: Aubé
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis*; D041901:Stemonaceae / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000470:Alkaloids; C441784:stenine