| 2-Deoxy-β-glycosides are found in many biologically active natural products, including antitumor compounds such as the landomycins, aureolic acids, and calicheamicins. The antitumor activity of these molecules is directly related to their ability to bind to specific sequences of DNA, with their deoxygenated glycosyl fragments serving as DNA recognition elements. During the course of my thesis research, I have developed a new family of 2-deoxy-2-iodo-glycosyl donors for synthesizing 2-deoxy-β-glycosides. This new class of glycosyl donors provides 2-deoxy-β-glycosides in high yields with excellent stereoselectivities. The highly deoxygenated and structurally complex hexasaccharide fragment of landomycin A was synthesized with excellent stereocontrol using this new methodology. |
