StaffsSeiichi Nakamura, Ph.D., Professor
Hiroyuki Yamakoshi, Ph.D., Research Associate
- Studies on the Synthesis of Biologically Active Natural Products
- Development of Efficient Methods for Construction of Molecular Architectures
- Development of Novel Asymmetric Reactions
Natural products have played a significant role in the development of organic chemistry, especially in the area of fine organic synthesis. Compounds with unprecedented molecular architecture and multiple functional groups have created opportunities for devising new strategies and methodologies as well as evaluating the synthetic utility of known methods and reactions. In addition, making target molecules in a practical fashion represents one of the major challenges in synthetic organic chemistry.
Our research has focused on the synthesis of biologically active natural products, and the development of new reactions and strategies for organic synthesis. We are also engaged in the development of novel asymmetric reactions that can be utilized for the facile preparation of enantiomerically pure compounds for drug discovery.
(1) We have accomplished the total synthesis of the calcium channel activator pinnatoxin A (left) by exploiting a tandem double hemiketal formation/hetero-Michael addition sequence to construct its [6,5,6]-dispiroketal ring system. Our first total synthesis of polygalolide A (right) by a carbonyl ylide cycloaddition strategy serves to provide stereochemical insight into the biosynthesis of this class of natural products.
(2) We recently developed a Ni-catalyzed asymmetric arylation of aromatic aldehydes using borane reagents, wherein ortho substitution was found to contribute to the excellent π-facial selectivity. Incorporation of a readily removable silyl group as a hydrogen surrogate expands the synthetic utility of the reaction.
Graduate School of Pharmaceutical Sciences, Nagoya City University
3-1 Tanabe-dori, Mizuho-ku, Nagoya 467-8603, Japan