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Total Synthesis of Ouabagenin and Ouabain

Authors

  • Hongxing Zhang Dr.,

    1. Laboratoire de synthèse organique Institut de Pharmacologie de Sherbrooke, Université de Sherbrooke, Sherbrooke, Québec, J1H 5N4, Canada, Fax: (+1) 819-820-6868
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  • Maddi Sridhar Reddy Dr.,

    1. Laboratoire de synthèse organique Institut de Pharmacologie de Sherbrooke, Université de Sherbrooke, Sherbrooke, Québec, J1H 5N4, Canada, Fax: (+1) 819-820-6868
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  • Serge Phoenix Dr.,

    1. Laboratoire de synthèse organique Institut de Pharmacologie de Sherbrooke, Université de Sherbrooke, Sherbrooke, Québec, J1H 5N4, Canada, Fax: (+1) 819-820-6868
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  • Pierre Deslongchamps Prof. Dr.

    1. Laboratoire de synthèse organique Institut de Pharmacologie de Sherbrooke, Université de Sherbrooke, Sherbrooke, Québec, J1H 5N4, Canada, Fax: (+1) 819-820-6868
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  • We thank Dr. Vijay Kumar for his assistance in providing starting materials. We also thank NSERCC (Ottawa) for financial support.

Abstract

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The highly oxygenated steroid ouabagenin (1 b) and its glycoside ouabain (1 a) 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 1 b in 27 steps. Finally, ouabagenin (1 b) was converted into ouabain (1 a) in six steps (see scheme).

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