title: Total synthesis of ouabagenin and ouabain.
abstract: A full account of the total synthesis of ouabagenin and ouabain is described. A highly stereocontrolled anionic cycloaddition for the rapid construction of the basic steroid skeleton is a pivotal conversion for the whole strategy. A careful study was needed to establish the order and the sequence of functional group manipulations. Specific conformational features of the ouabain skeleton allowed us to overcome a few stereochemical problems. Degradation studies on ouabain provided an ultimate proof for a key intermediate, which is used as a relay. Late stage butenolide formation and glycosidation yielded ouabain.
authors.affiliation: Laboratoire de Synthèse Organique, Département de Chimie, Institut de Pharmacologie de Sherbrooke, Université de Sherbrooke, Sherbrooke, Québec J1H 5N4, Canada.
authors.forename: Maddi Sridhar
authors.initials: MS
authors.lastname: Reddy
authors.forename: Hongxing
authors.initials: H
authors.lastname: Zhang
authors.forename: Serge
authors.initials: S
authors.lastname: Phoenix
authors.forename: Pierre
authors.initials: P
authors.lastname: Deslongchamps
mesh_terms: D015107:4-Butyrolactone / Q000031:analogs & derivatives / Q000737:chemistry; D018360:Crystallography, X-Ray; D003500:Cyclization; D010042:Ouabain / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry; D010084:Oxidation-Reduction; D013237:Stereoisomerism
chemical_list: D010042:Ouabain; C004511:butenolide; D015107:4-Butyrolactone; C008721:ouabagenin