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Synfacts 2008(6): 0562-0562  
DOI: 10.1055/s-2008-1072606
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Ouabain

Contributor(s): Philip Kocienski
H. Zhang, M. S. Reddy, S. Phoenix, P. Deslongchamps*
Université de Sherbrooke, Canada
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Publikationsdatum:
21. Mai 2008 (online)

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Significance

Ouabain is a cardioactive glycoside isolated from the African tree Acokanthera ouabio. It also occurs naturally in mammals as an endogenous digitalis. The Deslongchamps group accomplished the first total synthesis of ouabain and its aglycone ouabagenin which features a double-Michael addition followed by an aldol condensation to construct the tetracycle D.