Document Detail

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