Total synthesis of bioactive natural products

The development of pharmaceuticals and pesticides is often carried out through (1) search and selection of pipeline compounds with useful physiological effects such as natural products, (2) structural optimization by synthesis, and (3) clinical trials. It should be able to play a core role. Synthetic researcher should be able to play a core role. The medicines developed in this way have greatly contributed to the battle between humankind and infectious diseases. Moreover, even now, we do not know exactly the number of microorganisms present at our feet. Therefore, there are more types of microorganisms in nature than you can imagine, and they will continue to be a treasure trove of pharmaceutical compounds. Research on total synthesis of natural products has greatly contributed to the supply of pharmaceutical compounds, structure determination of natural products, elucidation of biosynthetic pathways, and discovery of new reactions, and plays an important role in both industrial and academic fields.

Synthetic study of amycolamicin, a potent broad-spectrum antibiotic

 Amycolamicin (AMM), which exhibits potent antibacterial activity including MRSA and VRE, was discovered from the soil actinomycete Amycolatopsis sp. MK575-fF5. The challenging molecular architecture of AMM prompted our efforts toward its total synthesis. We achieved total synthesis of AMM with a strikingly unique hybrid structure composed of five units by a convergent synthesis method. Having completed the total synthesis of AMM, our interest is now directed toward its structure-activity relationship studies.

Glycosyl Bunte Salts: A Class of Intermediates for Sugar Chemistry 

 We carried out the development of glycosylation with a method that overturns the conventional method, which is performed in water without using protecting groups. Specifically, we found that an unprecedented glycosyl bunte salt synthesized from unprotected sugar in the presence of a dehydration condensing agent and sodium thiosulfate. This reaction can be applied to unprotected oligosaccharides without any problem. Furthermore, we succeeded in synthesizing glycosyl thiol, which conventionally required a multi-step reaction, by reacting sodium sulfide with a glycosyl bunte salt in one step. We developed an epoch-making reaction with extremely high utility value by using glycosyl bunte salt as an intermediate.