| Strategic redox relay enables a scalable synthesis of ouabagenin, a bioactive cardenolide. | |
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MedLine Citation:
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PMID: 23288535 Owner: NLM Status: In-Data-Review |
Abstract/OtherAbstract:
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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. |
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Authors:
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Hans Renata; Qianghui Zhou; Phil S Baran |
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Publication Detail:
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Type: Journal Article; Research Support, N.I.H., Extramural; Research Support, Non-U.S. Gov't |
Journal Detail:
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Title: Science (New York, N.Y.) Volume: 339 ISSN: 1095-9203 ISO Abbreviation: Science Publication Date: 2013 Jan |
Date Detail:
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Created Date: 2013-01-04 Completed Date: - Revised Date: - |
Medline Journal Info:
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Nlm Unique ID: 0404511 Medline TA: Science Country: United States |
Other Details:
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Languages: eng Pagination: 59-63 Citation Subset: IM |
Affiliation:
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Department of Chemistry, The Scripps Research Institute, La Jolla, CA 92037, USA. |
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Descriptor/Qualifier:
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| Grant Support | |
ID/Acronym/Agency:
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CA134785/CA/NCI NIH HHS |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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