Abstract

The specific aims of this competitive renewal application are: (1) synthesis of aureolic acid antibiotics; (2) synthesis of aureolic acid analogs with improved DNA binding properties; (3) synthesis of the calicheamicin g1I aryl tetrasaccharide for use in as a DNA binding ligand; (4) development of new glycosidation reactions for application towards the solid-phase synthesis of oligosaccharides; and (5) completion of total syntheses of mycalamides A and B, and synthesis of mycalamide analogs.

  Funding Agency

Agency
National Institute of Health (NIH)
Institute
National Institute of General Medical Sciences (NIGMS)
Type
Research Project (R01)
Project #
2R01GM038907-08
Application #
2179608
Study Section
Special Emphasis Panel (ZRG3-BNP (01))
Project Start
1988-07-01
Project End
1999-08-31
Budget Start
1995-09-01
Budget End
1996-08-31
Support Year
8
Fiscal Year
1995
Total Cost
Indirect Cost

  Institution

Name
Indiana University Bloomington
Department
Chemistry
Type
Schools of Arts and Sciences
DUNS #
006046700
City
Bloomington
State
IN
Country
United States
Zip Code
47401

  Publications

Bates, Robert H; Shotwell, J Brad; Roush, William R (2008) Stereoselective syntheses of the C(1)-C(9) fragment of amphidinolide C. Org Lett 10:4343-6
Va, Porino; Roush, William R (2007) Total Synthesis of Amphidinolide E and Amphidinolide E Stereoisomers. Tetrahedron 63:5768-5796
Va, Porino; Roush, William R (2006) Total synthesis of amphidinolide E. J Am Chem Soc 128:15960-1
Lambert, William T; Roush, William R (2005) Synthesis of the A-B subunit of angelmicin B. Org Lett 7:5501-4
Tinsley, Jennifer M; Roush, William R (2005) Total synthesis of asimicin via highly stereoselective [3 + 2] annulation reactions of substituted allylsilanes. J Am Chem Soc 127:10818-9
Mertz, Eric; Tinsley, Jennifer M; Roush, William R (2005) [3 + 2]-annulation reactions of chiral allylsilanes and chiral aldehydes. studies on the synthesis of bis-tetrahydrofuran substructures of annonaceous acetogenins. J Org Chem 70:8035-46
Tinsley, Jennifer M; Mertz, Eric; Chong, Pek Y et al. (2005) Synthesis of (+)-bullatacin via the highly diastereoselective [3+2] annulation reaction of a racemic aldehyde and a nonracemic allylsilane. Org Lett 7:4245-8
Heitzman, Cheryl L; Lambert, William T; Mertz, Eric et al. (2005) Efficient protiodesilylation of unactivated C(sp3)-SiMe2Ph bonds using tetrabutylammonium fluoride. Org Lett 7:2405-8
Roush, William R; Neitz, R Jeffrey (2004) Studies on the synthesis of landomycin A. Synthesis of the originally assigned structure of the aglycone, landomycinone, and revision of structure. J Org Chem 69:4906-12
Shotwell, J Brad; Roush, William R (2004) Synthesis of the C11-C29 fragment of amphidinolide F. Org Lett 6:3865-8

Showing the most recent 10 out of 19 publications