Chemical glycosylation methods inspired by new biomimetic concepts and their application to natural products synthesis

CARB 102

Kazunobu Toshima, toshima@applc.keio.ac.jp, Department of Applied Chemistry, Faculty of Science and Technology, Keio University, 3-14-1 Hiyoshi, Kohoku-ku, Yokohama, 223-8522, Japan
The development of an efficient glycosylation method, which is one of the most fundamental and important transformation reactions of carbohydrates, is now becoming more and more important not only in carbohydrate chemistry, but also in synthetic organic chemistry. An efficient chemical glycosylation is a powerful tool to construct both natural and unnatural glycosides, and is urgently needed both in the laboratory and in industry. Herein, I will discuss the following three topics on chemical glycosylation reactions inspired by new biomimetic concepts and their application to natural products synthesis. 1. Practical glycosylations using DNA and RNA as glycosyl donors inspired by DNA alkylating agents in molecular biology. 2. Chemoselective glycosylations using 2,3-unsaturated sugars inspired by the reaction mechanism of lysozyme. 3. Synthetic studies of an antibiotic, vineomycin B2, by the application of chemoselective glycosylations.