The ultimate goal of our research is to design and develop highly efficient catalytic processes for the syntheses of biochemicals, which enable us to carry out multi-step synthesis using simple starting materials in one-pot in a highly organized manner. These highly efficient and sophisticated catalytic processes may eventually replace many conventional methods for the syntheses of pharmaceuticals and other biologically active compounds of medicinal interest. As the continuation of our approaches to this challenging goal, we will focus our efforts on the development of new and efficient catalytic synthetic processes for the asymmetric syntheses of heterocyclic and carbocyclic compounds of medicinal interest in the next funding period. The proposed research includes the following two projects. 1. Development of new and efficient methods for the synthesis of heterocycles and carbocycles of medicinal interest. In this project, we will perform extensive investigations on the development of new methodologies on catalytic annulation processes including reglo- and stereoselective cyclocarbonylations, directed silylformylations, and silylcarbocyclizations (SiCACs) for the syntheses Of heterocycles and carbocycles of medicinal interest. 2. Catalytic asymmetric synthesis of heterocyclic and carbocyclic compounds. In this project we plan to develop new catalytic asymmetric processes including asymmetric SiCAC reactions, asymmetric cyclocarbonylation of meso-dialkenylamines, and asymmetric hydroformylation, which will provide powerful methods for efficient asymmetric synthesis of biologically active heterocyclic and carbocyclic compounds. These new processes are promoted by rhodium complex catalysts with a variety of chiral phosphite ligands.

Agency
National Institute of Health (NIH)
Institute
National Institute of General Medical Sciences (NIGMS)
Type
Research Project (R01)
Project #
5R01GM039226-10
Application #
2749850
Study Section
Medicinal Chemistry Study Section (MCHA)
Project Start
1988-09-01
Project End
2000-07-31
Budget Start
1998-08-01
Budget End
2000-07-31
Support Year
10
Fiscal Year
1998
Total Cost
Indirect Cost
Name
State University New York Stony Brook
Department
Chemistry
Type
Schools of Arts and Sciences
DUNS #
804878247
City
Stony Brook
State
NY
Country
United States
Zip Code
11794
Ojima, Iwao (2013) Exploration of fluorine chemistry at the multidisciplinary interface of chemistry and biology. J Org Chem 78:6358-83
Chiou, Wen-Hua; Schoenfelder, Angele; Mann, Andre et al. (2008) Application of Rhodium-Catalyzed Cyclohydrocarbonylation to the Syntheses of Enantiopure Homokainoids. Pure Appl Chem 80:1019-1024
Chiou, Wen-Hua; Mizutani, Nobihiro; Ojima, Iwao (2007) Highly efficient synthesis of azabicyclo[x.y.0]alkane amino acids and congeners by means of Rh-catalyzed cyclohydrocarbonylation. J Org Chem 72:1871-82
Chiou, Wen-Hua; Schoenfelder, Angele; Sun, Liang et al. (2007) Rhodium-catalyzed cyclohydrocarbonylation approach to the syntheses of enantiopure homokainoids. J Org Chem 72:9418-25
Chapsal, Bruno D; Ojima, Iwao (2006) Total synthesis of enantiopure (+)-gamma-lycorane using highly efficient Pd-catalyzed asymmetric allylic alkylation. Org Lett 8:1395-8
Bennacer, Bibia; Fujiwara, Masaki; Lee, Seung-Yub et al. (2005) Silicon-initiated carbonylative carbotricyclization and [2+2+2+1] cycloaddition of enediynes catalyzed by rhodium complexes. J Am Chem Soc 127:17756-67