Total synthesis and biological evaluation of ustiloxin natural products and two analogs

Bioorg Med Chem Lett. 2006 Sep 15;16(18):4804-7. doi: 10.1016/j.bmcl.2006.06.071.

Pixu Li ¹, Cory D Evans, Erin M Forbeck, Haengsoon Park, Ruoli Bai, Ernest Hamel, M M Joullié

Affiliations

Affiliation

1 Department of Chemistry, University of Pennsylvania, 231 S. 34th Street, Philadelphia, PA 19104, USA.

PMID: 16837194 DOI: 10.1016/j.bmcl.2006.06.071

Abstract

Synthetic investigations of ustiloxin natural products are described. The first total synthesis of ustiloxin F was completed in 15 steps via ethynyl aziridine ring-opening by a phenol derivative. The results of biological tests of synthetic ustiloxins D and F, and two analogs, O-Me-ustiloxin D and 6-Ile-ustiloxin, demonstrated that the free hydroxyl group ortho to the ether linkage is critical for activity and variations at the Val/Ala site produce changes in the biological activity suggesting the need for further perturbations at this site to more extensively study the tubulin binding.

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