Abstract

This project concerns a study of the organotransition metal complexes as precursors to quinone compounds. Through such a study we hope to gain a better understanding of how to use organotransition metal species in the synthesis of complex organic molecules and at the same time develop general methods for quinone synthesis which will open up simple routes to anticancer quinones. Specifically, we have focused on the synthesis of maleoyl- and phthaloylmetal complexes and on their reaction with alkynes to give benzoquinones and naphthoquinones. We have been successful in developing simple synthesis of such complexes and in finding a general reaction with alkynes.

  Funding Agency

Agency
National Institute of Health (NIH)
Institute
National Cancer Institute (NCI)
Type
Research Project (R01)
Project #
5R01CA040157-03
Application #
3179719
Study Section
Metallobiochemistry Study Section (BMT)
Project Start
1979-07-01
Project End
1988-06-30
Budget Start
1986-07-01
Budget End
1987-06-30
Support Year
3
Fiscal Year
1986
Total Cost
Indirect Cost

  Institution

Name
Emory University
Department
Type
Schools of Arts and Sciences
DUNS #
042250712
City
Atlanta
State
GA
Country
United States
Zip Code
30322

  Publications

Yang, Hao; Li, Hao; Wittenberg, Rudiger et al. (2007) Ambient temperature synthesis of high enantiopurity N-protected peptidyl ketones by peptidyl thiol ester-boronic acid cross-coupling. J Am Chem Soc 129:1132-40
Aguilar-Aguilar, Angelica; Liebeskind, Lanny S; Pena-Cabrera, Eduardo (2007) Pd-catalyzed, Cu(I)-mediated cross-couplings of bisarylthiocyclobutenediones with boronic acids and organostannanes. J Org Chem 72:8539-42
Liu, Songbai; Yu, Ying; Liebeskind, Lanny S (2007) N-substituted imines by the copper-catalyzed N-imination of boronic acids and organostannanes with O-acyl ketoximes. Org Lett 9:1947-50
Egi, Masahiro; Liebeskind, Lanny S (2003) Heteroaromatic thioether-organostannane cross-coupling. Org Lett 5:801-2
Liebeskind, Lanny S; Srogl, Jiri (2002) Heteroaromatic thioether-boronic acid cross-coupling under neutral reaction conditions. Org Lett 4:979-81
Savarin, Cecile; Srogl, Jiri; Liebeskind, Lanny S (2002) A mild, nonbasic synthesis of thioethers. The copper-catalyzed coupling of boronic acids with N-thio(alkyl, aryl, heteroaryl)imides. Org Lett 4:4309-12
Deng, X; Liebeskind, L S (2001) A contribution to the design of molecular switches: novel acid-mediated ring-closing--photochemical ring-opening of 2,3-bis(heteroaryl)quinones (heteroaryl = thienyl, furanyl, pyrrolyl). J Am Chem Soc 123:7703-4
Savarin, C; Srogl, J; Liebeskind, L S (2001) Substituted alkyne synthesis under nonbasic conditions: copper carboxylate-mediated, palladium-catalyzed thioalkyne-boronic acid cross-coupling. Org Lett 3:91-3
Savarin, C; Liebeskind, L S (2001) Nonbasic, room temperature, palladium-catalyzed coupling of aryl and alkenyl iodides with boronic acids mediated by copper(I) thiophene-2-carboxylate (CuTC). Org Lett 3:2149-52
Savarin, C; Srogl, J; Liebeskind, L S (2000) Thiol ester-boronic acid cross-coupling. Catalysis using alkylative activation of the palladium thiolate intermediate. Org Lett 2:3229-31

Showing the most recent 10 out of 12 publications