RESEARCH
Research Policy
Many of the functional molecules such as pharmaceuticals, pesticides, cosmetics, chemical fibers and organic electroluminescent devices, which are indispensable for us to lead a prosperous life, are mainly organic molecules. "Molecular transformation" is a powerful synthetic method required to assemble organic molecules, and is a scientific technology that forms the basis of manufacturing. The Shimada research group aim to contribute to the realization of a sustainable society by conducting the development of "organic reactions" and "synthetic methods" based on the creation of the unique "molecular catalysts" or "synthetic reagents".
Research Subject
Development of Molecular Catalysts
In principle, a catalysis that can produce an infinite number of products from a single catalyst is the most ideal molecular transformation from the viewpoint of efficiency. In addition, catalysis is an environmental friendly scientific technology because it can effectively utilize resources and energy. Our research group has been focused on the development of effective molecular catalysts for synthesizing bioorganic molecules such as peptides and sugar chains. In this context, we have succeeded in the development of organoboron catalysts utilizing the characteristic features of organic boronic acid derivatives that form areversible covalent bonds via dehydration by the reaction with alcohols and carboxylic acids. We will continue to develop unique molecular catalysts with the aim of realizing useful molecular transformations.
Development of Synthetic Reagents
Our research group is also working on the development of synthetic reagents to achieve useful molecular transformations. Research progress in synthetic organic chemistry have led to the development of many molecular transformations that achieve high stereoselectivity and high regioselectivity. However, suppression of undesired side reactions is still required in chemical synthesis of complex molecules. In such situations, the use of protecting groups is very effective.Our research group has been focused on the development of easily removable protecting groups under mild reaction conditions. In this context, we have succeeded the developmet of a protective agent for diols utilizing the unique property that structurally modified boronic acid improves the stability of the corresponding boronic acid ester. We will continue to the development of unique synthetic reagents with the aim of realizing useful molecular transformations.
Synthetic Application of Catalysis and Methodologies
To demonstrate of synthetic utilities of our catalysis and methodologies, we are conducting applied research on the chemical synthesis of useful molecules. We have achieved the synthesis of pharmaceuticals and biologically active acyloin natural products using catalytic dehydrative amidation reactions, the synthesis of partially acylated natural products using catalytic regioselective acylation of cabohydrates, and the total synthesis of sulfated glycolipids utilizing the diol protective agent , so far. In all cases, we have succeeded in establishing a more efficient and environmentally friendly synthetic routes compared to the conventional reports. We will continue to aim the establishment of practical process chemistry by applying the molecular transformations that we have developed.
