We propose to synthesize five representative members of the biologically important class of naturally-occurring polyethers, including the antibiotics septamycin, nigericin, lasalocid A, and ionomycin, and the algal metabolite thyrsiferol. Versatile stereoselective methods for producing substituted tetrahydrofurans and tetrahydropyrans by cyclization of olefinic alcohol derivatives with relative asymmetric induction will be developed. These methods involve electrophilic cyclization of ether derivatives and hydroperioxides (for the selective formation of cis-2,5-disubstituted tetrahydrofurans) and cyclization of the alcohols themselves or ring contraction of tetrahydropyrans (for the selective formation of the trans-isomers).

Agency
National Institute of Health (NIH)
Institute
National Institute of General Medical Sciences (NIGMS)
Type
Research Project (R01)
Project #
5R01GM030141-04
Application #
3277751
Study Section
Medicinal Chemistry Study Section (MCHA)
Project Start
1982-02-01
Project End
1987-01-31
Budget Start
1985-02-01
Budget End
1986-01-31
Support Year
4
Fiscal Year
1985
Total Cost
Indirect Cost
Name
University of California Berkeley
Department
Type
Schools of Arts and Sciences
DUNS #
094878337
City
Berkeley
State
CA
Country
United States
Zip Code
94704