A convergent total synthesis of ouabagenin. Issue 6 (16th April 2015)

• Record Type: Journal Article
• Authors: Mukai, Ken; Kasuya, Satoshi; Nakagawa, Yuki; Urabe, Daisuke; Inoue, Masayuki
• Is Part Of: Chemical science. Volume 6:Issue 6(2015:Jun.)
• Page Start: 3383
• Page End: 3387
• Publication Date: 2015-04-16
• Subjects: Chemistry -- Periodicals; 540.5
• DOI: 10.1039/c5sc00212e
• Languages: English
• ISSNs: 2041-6520

Abstract

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. 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.