A convergent total synthesis of ouabagenin
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Authors: | Ken Mukai Satoshi Kasuya Yuki Nakagawa Daisuke Urabe Masayuki Inoue |
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Affiliation: | a Graduate School of Pharmaceutical Sciences , The University of Tokyo , Hongo , Bunkyo-ku , Tokyo 113-0033 , Japan . Email: |
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Abstract: | A convergent total synthesis of ouabagenin, an aglycon of cardenolide glycoside ouabain, was achieved by assembly of the AB-ring, D-ring and butenolide moieties. The multiply oxygenated cis-decalin structure of the AB-ring was constructed from (R)-perillaldehyde through the Diels–Alder reaction and sequential oxidations. The intermolecular acetal formation of the AB-ring and D-ring fragments, and combination of the intramolecular radical and aldol reactions, assembled the requisite steroidal skeleton in a stereoselective fashion. Finally, stereoselective installation of the C17-butenolide via the Stille coupling and hydrogenation led to ouabagenin. |
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