ORGN 166 |
| Pleuromutilin, isolated from Pleurotus species, is a representative diterpene mutilin antibiotic. The antibacterial activity level of pleuromutilin against methicillin-resistant Staphylococcus aureus (MRSA) is as high as that of vancomycin. In the present study, as part of an ongoing effort to develop a novel mutilin antibiotic, we focused on the synthesis of C-20 modified analogues. Stereoselective alkylation at the C-12 position of de-ethenylated mutilin was found to be a key methodology for the synthesis of C-20 substituted mutilins. Indeed, C-12 alkylated mutilins were successfully converted to the C-20 substituted mutilins bearing a fluoro, methyl, or trifluoromethyl group at the C-20 position by way of dehydrosulfenylation, alkyne isomerization, or trifluoromethylation.
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Total Synthesis, Materials, Devices and Switches, Molecular Recognition and Self-Assembly, Biologically-Related Molecules and Processes
8:00 PM-10:00 PM, Sunday, August 19, 2007 BCEC -- Exhibit Hall - B2, Poster
Division of Organic Chemistry |
