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1. Total synthesis of the antifungal dilactones UK-2A and UK-3A: The determination of their relative and absolute configurations, analog synthesis and antifungal activities

Author

Hisato Senda, Kiyoshi Inoguchi, Takashi Ikari, Tetsuo Shibata, Nobuko Itoh, Noriyuki Kamei, and Masanao Shimano

Subjects
Antifungal, Analog synthesis, Antifungal antibiotic, medicine.drug_class, Chemistry, Organic Chemistry, Enantioselective synthesis, Total synthesis, Ring (chemistry), Selective cytotoxicity, Biochemistry, Combinatorial chemistry, Drug Discovery, medicine
Abstract

The synthesis of the antifungal dilactones, UK-2A and UK-3A, is described. In addition to providing a workable synthetic route to these potent antifungal antibiotics, this has allowed us to determine the assignment of the relative and absolute configurations in the nine-membered ring. Furthermore, UK-2A analogs were also synthesized and evaluated their antifungal activities and cytotoxic activities along with UK-2A, (2R, 3R, 4S, 7R)-UK-2A, UK-3A, (2R, 3R, 4S, 7R)-UK-3A, and antimycin A. The structural requirements for the selective cytotoxicity against yeasts and filamentous fungi will also be suggested.

Published
1998
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