Total Synthesis of the Monomeric Unit of Lomaiviticin A

The architecturally symmetrical and synthetically challenging marine natural products lomaiviticins A and B present alluring synthetic targets due to their molecular complexity, potent antitumor properties, and natural scarcity. Herein, we report the total synthesis of the fully glycosylated monomer...

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Bibliographic Details
Published in:Journal of the American Chemical Society 2020-11, Vol.142 (47), p.20201-20207
Main Authors: Nicolaou, K. C, Chen, Qifeng, Li, Ruofan, Anami, Yasuaki, Tsuchikama, Kyoji
Format: Article
Language:English
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Summary:The architecturally symmetrical and synthetically challenging marine natural products lomaiviticins A and B present alluring synthetic targets due to their molecular complexity, potent antitumor properties, and natural scarcity. Herein, we report the total synthesis of the fully glycosylated monomeric unit of lomaiviticin A, monolomaiviticin A. The retrosynthetically derived synthetic strategy relied on an intramolecular palladium-catalyzed coupling reaction to complete the tetracyclic aglycon scaffold and gold-promoted glycosylations to install the synthetically challenging α- and β-glycoside moieties of the target molecule. This accomplishment paves a path for the eventual total synthesis of lomaiviticins A and B and opens opportunities for biological investigations within this family of compounds.
ISSN:0002-7863
1520-5126
DOI:10.1021/jacs.0c10660