ORGN 478 |
| Marlenne Mulero, David Rodriguez, and José A. Prieto. Department of Chemistry, University of Puerto Rico, PO Box 23346, San Juan, PR 00931-3346 |
| The macrolides continue to be of interest to the synthetic community because of their biological activities and their synthetic challenge. Bafilomycin A1 is a macrolide which exhibit antibacterial and antifungal activity, and is the first specific inhibitor of vacuolar H+ATPase. Its structure consists of a 16-membered macrolide that contains a tetraene core, a polypropionate chain, and 12 stereogenic centers. We are focused on the preparation of the C13-C25 segment of Bafilomycin A1 in a convergent approach by coupling epoxides 1 and 2. The methodology which consists on the stereoselective preparation of epoxides and their regioselective cleavage with alkynyl alanes to generate carbon-carbon bonds, has been applied in a reiterative fashion. A sequence of a stereoselective alkyne reduction, epoxidation, and epoxide cleavage was used to generate a propionate unit with the required relative configuration. Supported by the NIH SCORE 2S06GM-08102-29, NIH RISE (1R25-GM-61151-01A1) |
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Total Synthesis, Asymmetric Reactions and Syntheses, Bioorganic
9:00 AM-11:00 AM, Wednesday, March 31, 2004 Anaheim Convention Center -- Hall C, Poster
Sci-Mix
Division of Organic Chemistry |
