TOTAL SYNTHESIS OF THE ANTIFUNGAL DILACTONES UK-2A AND UK-3A - THE DETERMINATION OF THEIR RELATIVE AND ABSOLUTE-CONFIGURATIONS, ANALOG SYNTHESIS AND ANTIFUNGAL ACTIVITIES

Authors
SHIMANO M KAMEI N SHIBATA T INOGUCHI K ITOH N IKARI T SENDA H
Citation
M. Shimano et al., TOTAL SYNTHESIS OF THE ANTIFUNGAL DILACTONES UK-2A AND UK-3A - THE DETERMINATION OF THEIR RELATIVE AND ABSOLUTE-CONFIGURATIONS, ANALOG SYNTHESIS AND ANTIFUNGAL ACTIVITIES, Tetrahedron, 54(42), 1998, pp. 12745-12774
Citations number
33
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
54
Issue
42
Year of publication
1998
Pages
12745 - 12774
Database
ISI
SICI code
0040-4020(1998)54:42<12745:TSOTAD>2.0.ZU;2-Z
Abstract
The synthesis of the antifungal dilactones, UK-2A and UK-3A, is descri bed. In addition to providing a workable synthetic route to these pote nt antifungal antibiotics, this has allowed us to determine the assign ment of the relative and absolute configurations in the nine-membered ring. Furthermore, UK-2A analogs were also synthesized and evaluated t heir 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 y easts and filamentous fungi will also be suggested. (C) 1998 Elsevier Science Ltd. All rights reserved.