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 need
Reddy, Maddi Sridhar,Zhang, Hongxing,Phoenix, Serge,Deslongchamps, Pierre
supporting information; experimental part
p. 725 - 741
(2011/06/25)
Total synthesis of ouabagenin and ouabain
(Chemical Equation Presented) The highly oxygenated steroid ouabagenin (1b) and its glycoside ouabain (1a) were prepared by a strategy based on a polyanionic cyclization. Starting building blocks A and B were combined to give the key intermediate C and transformed into 1b in 27 steps. Finally, ouabagenin (1b) was converted into ouabain (1a) in six steps (see scheme).
Zhang, Hongxing,Sridhar Reddy, Maddi,Phoenix, Serge,Deslongchamps, Pierre
p. 1272 - 1275
(2008/12/22)
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