Partial Synthesis of the Tetrasaccharide Fragment of Arugomycin
Trotta, Adam H.
2012
- Arugomycin is a biologically active natural product, showing both antibacterial and antitumor activities. It intercalates in DNA, binding to both the major and minor grooves. The two oligosaccharide chains play important roles in stabilizing the arugomycin-DNA complex. In recent years the Bennett lab has pioneered a strategy for cyclopropenium cation promoted dehydrative glycosylations of 2-deoxy ... read moresugars. With that in mind, a synthetic strategy was outlined for the synthesis of the tetrasaccharide fragment of arugomycin. This structure would be difficult to access using traditional glycosylation methods, highlighting the utility of the cyclopropenium cation methodology. / The synthetic strategy revealed a common intermediate in the synthesis of all four monomers. The common intermediate was successfully synthesized. Three of the four monomers are functionalized with a methyl ether at C-3. Regioselective alkylation of the diol intermediate proved difficult, delaying the synthesis considerably. After several attempts at methylating the fucal, a new synthetic strategy was devised. Regioselective methylation was successfully completed on a 2-deoxy-fucopyranosyl derivative. /read less
- ID:
- 4m90f665m
- Component ID:
- tufts:UA005.015.019.00001
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