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Development of a concise synthesis of ouabagenin and hydroxylated corticosteroid analogues.

ABSTRACT: 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.

SUBMITTER: Renata H

PROVIDER: S-EPMC4353025 | biostudies-literature | 2015 Jan

REPOSITORIES: biostudies-literature

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Development of a concise synthesis of ouabagenin and hydroxylated corticosteroid analogues.

Renata Hans H Zhou Qianghui Q Dünstl Georg G Felding Jakob J Merchant Rohan R RR Yeh Chien-Hung CH Baran Phil S PS

Journal of the American Chemical Society 20150116 3

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 ...[more]

PMID: 25594682

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