ORGN 353 |
| Polypropionates are a common feature of many macrolides and ionophores possessing significant biological activities. For example, bafilomycin A1, our target compound, is a macrolide that exhibits antibacterial and antifungal activity, and is the first specific inhibitor of vacuolar H+ATPase. The synthesis of polypropionates has been extensively studied using different methodologies. Recently, we developed an iterative methodology for the preparation of polypropionates based on oxirane chemistry. This methodology entails a sequence of an alkyne reduction, a stereoselective epoxidation, and a regioselective epoxide cleavage to generate each propionate unit with the required relative configuration. In this work, we are focused on the preparation of the C13-C25 polypropionate segment (3) of bafilomycin A1 using a similar methodology, but in a convergent fashion. The studies on the stereoselective preparation of epoxides 1 and 2 and their coupling to generate 3 will be presented.
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New Reactions and Methodology, Bioorganic Chemistry, Molecular Recognition and Self Assembly
8:00 PM-10:00 PM, Tuesday, 28 March 2006 Georgia World Congress Center -- Ex. Hall B4, Poster
Sci-Mix
Division of Organic Chemistry |
