A plan is proposed, based on successful preliminary investigation, to reach chiral, enantiomerically pure, biologically active compounds or key precursors to these materials. By use of chiral bicyclic lactams, prepared from Gamma- or Delta-ketoacids or aldehyde acids and (S)-valinol, we hope to introduce, in an enantioselective manner, a variety of substituents to form a chiral quaternary center. This methodology will be used to prepare optically active precursors to the Amaryllidaceae, Aspidosperma, and Erythrina alkaloids, insect pheromones (Grandisol, Anistrephin), and octalones for steroid synthesis. In addition a number of useful compounds containing chirality due to the quaternary center will be prepared.

Agency
National Institute of Health (NIH)
Institute
National Institute of General Medical Sciences (NIGMS)
Type
Research Project (R01)
Project #
5R01GM034275-02
Application #
3284962
Study Section
Medicinal Chemistry Study Section (MCHA)
Project Start
1985-01-01
Project End
1987-12-31
Budget Start
1986-01-01
Budget End
1986-12-31
Support Year
2
Fiscal Year
1986
Total Cost
Indirect Cost
Name
Colorado State University-Fort Collins
Department
Type
Schools of Arts and Sciences
DUNS #
112617480
City
Fort Collins
State
CO
Country
United States
Zip Code
80523
Resek, James E (2008) Intramolecular ene reaction of a chiral bicyclic lactam. J Org Chem 73:9792-4