The ultimate goal of our research is to design and develop highly efficient catalytic processes for the syntheses of enantiopure biochemicals, which enable us to carry out multi-step synthesis from simple starting materials in a highly organized manner. These highly efficient and sophisticated catalytic processes, especially catalytic asymmetric transformations, 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 synthesis of heterocyclic and carbocyclic compounds of medicinal interest in the next funding period. The proposed research includes the following two specific aims. 1. Development of new and efficient catalytic methods and catalytic asymmetric processes for the syntheses of heterocycles and carbocycles. In this project, we will perform extensive investigations on the development of new methodologies on catalytic annulation processes including regio-, stereo-, and enantioselective directed hydrosilylations, directed silylformylations, silylcarbocyclizations (SiCaCs), and cyclohydrocarbonylations for the synthesis of heterocycles and carbocycles. 2. Asymmetric synthesis of heterocyclic, carbocyclic, and related compounds of medicinal interest. In this project, we plan to develop new synthetic routes to a variety of enantiopure heterocyclic and carbocyclic compounds of medicinal interest featuring diastereoselective or enantioselective catalytic processes as the key steps.

Agency
National Institute of Health (NIH)
Institute
National Institute of General Medical Sciences (NIGMS)
Type
Research Project (R01)
Project #
5R01GM039226-13
Application #
6625065
Study Section
Medicinal Chemistry Study Section (MCHA)
Program Officer
Schwab, John M
Project Start
1988-09-01
Project End
2005-11-30
Budget Start
2002-12-01
Budget End
2005-11-30
Support Year
13
Fiscal Year
2003
Total Cost
$259,667
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