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J Am Chem Soc. 2015 Jan 28;137(3):1330-40. doi: 10.1021/ja512022r. Epub 2015 Jan 16.

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

Author information

1
Department of Chemistry, The Scripps Research Institute , 10550 North Torrey Pines Road, La Jolla, California 92037, United States.

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.

PMID:
25594682
PMCID:
PMC4353025
DOI:
10.1021/ja512022r
[Indexed for MEDLINE]
Free PMC Article

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