Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 143, Issue 4, Pages 2138-2155Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.0c12569
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Funding
- University of Illinois
- Bristol-Myers Squibb
- National Science Foundation
- Amgen
- Eli Lilly
- FMC
- Roy J. Carver Charitable Trust, Muscatine, Iowa, USA
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The article discusses the structures, total syntheses, and cytotoxic activity studies of the isomalabaricanes, highlighting the importance of the core structure for their biological activity.
The isomalabaricanes comprise a large family of marine triterpenoids with fascinating structures that have been shown to be selective and potent apoptosis inducers in certain cancer cell lines. In this article, we describe the successful total syntheses of the isomalabaricanes stelletin A, stelletin E, and rhabdastrellic acid A, as well as the development of a general strategy to access other natural products within this unique family. High-throughput experimentation and computational chemistry methods were used in this endeavor. A preliminary structure-activity relationship study of stelletin A revealed the trans-syn-trans core motif of the isomalabaricanes to be critical for their cytotoxic activity.
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