Abstract

The principal objectives of this project are to design and execute enantioselective syntheses of the ionophore antibiotics lysocellin, ferensimycin, alborixin and X-206. During the course of this project the absolute configuration of both classes of ionophores will be unequivocally determined by chemical methods. The synthesis studies described above will rely heavily upon evoling concepts being developed in this laboratory in the area of asymmetric induction. Related new chemical concepts relevant to the general issue of stereochemical control in acyclic systems will be addressed. The long range goals of this research pertain to the rational design of poly-ligating organic molecules which can be employed as selective membrane ion carriers and chiral catalysts.

  Funding Agency

Agency
National Institute of Health (NIH)
Institute
National Institute of General Medical Sciences (NIGMS)
Type
Research Project (R01)
Project #
5R01GM033327-03
Application #
3282900
Study Section
Medicinal Chemistry Study Section (MCHA)
Project Start
1983-08-01
Project End
1986-11-30
Budget Start
1985-08-01
Budget End
1986-11-30
Support Year
3
Fiscal Year
1985
Total Cost
Indirect Cost

  Institution

Name
Harvard University
Department
Type
Schools of Arts and Sciences
DUNS #
071723621
City
Cambridge
State
MA
Country
United States
Zip Code

  Publications

Evans, David A; Nagorny, Pavel; McRae, Kenneth J et al. (2007) Enantioselective synthesis of oasomycin a, part I: synthesis of the C1-C12 and C13-C28 subunits. Angew Chem Int Ed Engl 46:537-40
Scheerer, Jonathan R; Lawrence, Jonathan F; Wang, Grace C et al. (2007) Asymmetric synthesis of salvinorin A, a potent kappa opioid receptor agonist. J Am Chem Soc 129:8968-9
Evans, David A; Nagorny, Pavel; McRae, Kenneth J et al. (2007) Enantioselective synthesis of oasomycin A, part III: fragment assembly and confirmation of structure. Angew Chem Int Ed Engl 46:545-8
Evans, David A; Nagorny, Pavel; Reynolds, Dominic J et al. (2007) Enantioselective synthesis of oasomycin A, part II: synthesis of the C29-C46 subunit. Angew Chem Int Ed Engl 46:541-4
Evans, David A; Nagorny, Pavel; Xu, Risheng (2006) Ceric ammonium nitrate promoted oxidation of oxazoles. Org Lett 8:5669-71
Evans, David A; Glorius, Frank; Burch, Jason D (2005) Complex aldol reactions for the construction of dense polyol stereoarrays: synthesis of the C33-C36 region of aflastatin A. Org Lett 7:3331-3
Evans, David A; Trenkle, William C; Zhang, Jing et al. (2005) Synthesis and confirmation of the absolute stereochemistry of the (-)-aflastatin a C9-C27 degradation polyol. Org Lett 7:3335-8
Evans, David A; Siska, Sarah J; Cee, Victor J (2003) Resurrecting the Cornforth model for carbonyl addition: studies on the origin of 1,2-asymmetric induction in enolate additions to heteroatom-substituted aldehydes. Angew Chem Int Ed Engl 42:1761-5
Evans, David A; Rajapakse, Hemaka A; Chiu, Anna et al. (2002) Asymmetric syntheses of pectenotoxins-4 and -8, part II: synthesis of the C20-C30 and C31-C40 subunits and fragment assembly. Angew Chem Int Ed Engl 41:4573-6
Evans, David A; Starr, Jeremy T (2002) A cascade cycloaddition strategy leading to the total synthesis of (-)-FR182877. Angew Chem Int Ed Engl 41:1787-90

Showing the most recent 10 out of 15 publications