Summary of Research Project Results under JSPS FY2003
"Research for the Future Program"

1.Research Institution The University of Tokyo
2.University-Industry Cooperative Research Committee 116th Committee on Chemistry Creating Organic Compounds with Novel Functions
3.Term of Project FY 1999 - FY 2003
4.Project Number 99R11601
5.Title of Project Creation of Supramolecular Assembly and Application to Development of Chemical Processes and Medicinal Lead Compounds

6.Project Leader
Name InstitutionCDepartment Title of Position
Masakatsu, Shibasaki The University of Tokyo , Graduate School of Pharmaceutical Sciences Professor

7.Core Members

Names Institution,Department Title of Position
Soutaro, Miyano Tohoku University, Graduate School of Engineering Professor
Norio, Teramae Tohoku University, Graduate School of Science Professor
Takuzo, Aida The University of Tokyo, Graduate School of Engineering Professor

8.Summary of Research Results

On the sub-project of "Development of Environmentally Benign Synthesis Using Supramolecular Catalysis", we developed a chiral heteropolymetallic complex containing a lanthanide metal, alkali metal, and BINOL. This new catalyst promotes the direct enantioselective aldol reaction from unmodified ketones and aldehydes with high enantioselectivity. We also developed a novel chiral logand, linked BINOL, and found that the zinc complex can promote very efficient C-C bond formation between a hydroxyl ketone and aldehydes or imines. The maximum catalyst turn-over was reached up to 20000 with maintaining an excellent enantioselectivity. Moreover, we developed a new sugar-derived catalyst that can promote enantioselective cyanosilylation of ketones and ketoimines with high efficiency. Using these catalysis, we established efficient synthetic route of camptothecin (anticancer drug), oxybutynin (muscarinic receptor antagonist), and sorbinil (aldose reductase inhibitor). These syn thetic route have a potential of being applied to industrial synthesis.
On the sub-project of "Development of Supramolecular Bio-Response System", we synthesized a calix-arene molecule displaying D-glucose, and found that this molecule demonstrates a very strong hydrogen-bonding ability. This molecule can carry a guest molecule inside to a targeted place.

9.Key Words
(1)asymmetric catalyst   (2)enbironmentally benign synthesis   (3)supramolecular catalyst
(4)self assembly   (5)industrial synthesis   (6)atom-economy
(7)biologic activity   (8)pharmaceutical synthesis   (9)molecular recognition