Abstract

The proposed research consists of the first nonracemic synthesis of Roseophilin. Roseophilin has been shown to have potent cytotoxic properties against K562 human erythroid leukemia and KB human epidermoid cells. The proposed total synthesis will involve a chiral tetrazine Diels-Alder reaction, McMurry reductive carbonyl coupling, and acyl radical-alkene ring closing as the key steps. Based on structural relationships to a family of similar cytotoxic compounds, a linker will be attached in an effort to identify Roseophilin's biological target.

  Funding Agency

Agency
National Institute of Health (NIH)
Institute
National Cancer Institute (NCI)
Type
Postdoctoral Individual National Research Service Award (F32)
Project #
5F32CA086475-02
Application #
6362772
Study Section
Bio-Organic and Natural Products Chemistry Study Section (BNP)
Program Officer
Lohrey, Nancy
Project Start
2001-03-16
Project End
Budget Start
2001-03-16
Budget End
2002-03-15
Support Year
2
Fiscal Year
2001
Total Cost
$34,832
Indirect Cost

  Institution

Name
Scripps Research Institute
Department
Type
DUNS #
City
La Jolla
State
CA
Country
United States
Zip Code
92037

  Publications

Elliott, Gregory I; Fuchs, James R; Blagg, Brian S J et al. (2006) Intramolecular diels-alder/1,3-dipolar cycloaddition cascade of 1,3,4-oxadiazoles. J Am Chem Soc 128:10589-95
Wilkie, Gordon D; Elliott, Gregory I; Blagg, Brian S J et al. (2002) Intramolecular Diels-Alder and tandem intramolecular Diels-Alder/1,3-dipolar cycloaddition reactions of 1,3,4-oxadiazoles. J Am Chem Soc 124:11292-4