508-52-1Relevant articles and documents
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Tamm
, p. 147,158 (1955)
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A convergent total synthesis of ouabagenin
Mukai, Ken,Kasuya, Satoshi,Nakagawa, Yuki,Urabe, Daisuke,Inoue, Masayuki
, p. 3383 - 3387 (2015)
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. This journal is
Development of a concise synthesis of ouabagenin and hydroxylated corticosteroid analogues
Renata, Hans,Zhou, Qianghui,Dünstl, Georg,Felding, Jakob,Merchant, Rohan R.,Yeh, Chien-Hung,Baran, Phil S.
supporting information, p. 1330 - 1340 (2015/02/19)
The natural product ouabagenin is a complex cardiotonic steroid with a highly oxygenated skeleton. This full account describes the development of a concise synthesis of ouabagenin, including the evolution of synthetic strategy to access hydroxylation at the C19 position of a steroid skeleton. In addition, approaches to install the requisite butenolide moiety at the C17 position are discussed. Lastly, methodology developed in this synthesis has been applied in the generation of novel analogues of corticosteroid drugs bearing a hydroxyl group at the C19 position.(Chemical Equation Presented).
Strategic redox relay enables A scalable synthesis of ouabagenin, a bioactive cardenolide
Renata, Hans,Zhou, Qianghui,Baran, Phil S.
, p. 59 - 63 (2013/03/13)
Here, we report on a scalable route to the polyhydroxylated steroid ouabagenin with an unusual take on the age-old practice of steroid semisynthesis. The incorporation of both redox and stereochemical relays during the design of this synthesis resulted in efficient access to more than 500 milligrams of a key precursor toward ouabagenin-and ultimately ouabagenin itself-and the discovery of innovative methods for carbon-hydrogen (C-H) and carbon-carbon activation and carbon-oxygen bond homolysis. Given the medicinal relevance of the cardenolides in the treatment of congestive heart failure, a variety of ouabagenin analogs could potentially be generated from the key intermediate as a means of addressing the narrow therapeutic index of these molecules. This synthesis also showcases an approach to bypass the historically challenging problem of selective C-H oxidation of saturated carbon centers in a controlled fashion.
