[引用][C] Total synthesis of ouabagenin and ouabain

H Zhang, M Sridhar Reddy, S Phoenix… - Angewandte Chemie …, 2008 - Wiley Online Library
Ouabain (1a), a cardioactive glycoside isolated from the bark of the African ouabio tree
(Acokanthera ouabio) by Arnaud in 1888),[1] has received considerable attention since it
was discovered that an ouabain-like compound occurs naturally in mammals and acts as an
endogenous digitalis as proposed by Szent–Gyorgyi.[2] After some debate, it was
established that the endogenous and plant derived ouabain are in fact identical.[3]
Ouabagenin (1b), the aglycone of ouabain, was isolated for the first time in 1942 by Mannich …

Total synthesis of ouabagenin and ouabain

MS Reddy, H Zhang, S Phoenix… - Chemistry–An Asian …, 2009 - Wiley Online Library
All done! A full account of the total synthesis of ouabagenin and ouabain has been
described. The synthesis was achieved through a polyanionic cyclization strategy.
Degradation studies provide an ultimate proof for a key intermediate observed in the
synthesis. 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 …
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