Synthetic Studies on Selective, Proapoptotic Isomalabaricane Triterpenoids Aided by Computational Techniques

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...

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Published inJournal of the American Chemical Society Vol. 143; no. 4; pp. 2138 - 2155
Main Authors Boyko, Yaroslav D, Huck, Christopher J, Ning, Shang, Shved, Alexander S, Yang, Cheng, Chu, Tiffany, Tonogai, Emily J, Hergenrother, Paul J, Sarlah, David
Format Journal Article
LanguageEnglish
Published United States American Chemical Society 03.02.2021
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Summary: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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ISSN:0002-7863
1520-5126
DOI:10.1021/jacs.0c12569