Total synthesis of ouabagenin and ouabain.
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.
Reddy
Maddi Sridhar
MS
Laboratoire de Synthèse Organique, Département de Chimie, Institut de Pharmacologie de Sherbrooke, Université de Sherbrooke, Sherbrooke, Québec J1H 5N4, Canada.
Zhang
Hongxing
H
Phoenix
Serge
S
Deslongchamps
Pierre
P
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
D010042:Ouabain; C004511:butenolide; D015107:4-Butyrolactone; C008721:ouabagenin