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Issue 6, 2015
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A convergent total synthesis of ouabagenin

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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.

Graphical abstract: A convergent total synthesis of ouabagenin

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Publication details

The article was received on 20 Jan 2015, accepted on 28 Mar 2015 and first published on 30 Mar 2015


Article type: Edge Article
DOI: 10.1039/C5SC00212E
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Chem. Sci., 2015,6, 3383-3387
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    A convergent total synthesis of ouabagenin

    K. Mukai, S. Kasuya, Y. Nakagawa, D. Urabe and M. Inoue, Chem. Sci., 2015, 6, 3383
    DOI: 10.1039/C5SC00212E

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