Natural product synthesis, method development, and organometallics

Research in our group is focused on the development of transition metal catalyzed methods and their application to the total synthesis of complex molecules with promising biological activities. Specifically, we are interested in developing new reactions that have the potential to open avenues for forming carbon-carbon bonds and carbon-nitrogen bonds. For example, functionalization of carbon-hydrogen bonds catalyzed by late transition metals could allow for untraditional bond disconnections in constructing molecules. Such processes could enable the direct conversion of a carbon-hydrogen bond to a carbon-metal bond, which could be further transformed to a carbon-carbon bond or carbon-nitrogen bond. Additionally, we are interested in harnessing the potential of nitrogen radicals to form carbon-nitrogen bonds. Despite their potential, the use of these species in the preparation of nitrogen-containing compounds has been limited. This is likely due to several factors, such as the limited number of available precursors, the requirement of Bu3SnH as a reagent, and the need for special conditions such as photolysis or strongly acidic conditions. Some natural products, such as those shown below, possess unique molecular architectures and interesting biological properties. As we develop new methods, we plan to pursue these targets and highlight our chemistry.

Prior to the University of Arkansas

11. Tsang, W. C. P.; Munday, R.; Gordon, B.; Zheng, N.; Buchwald, S. L. “A Palladium-Catalyzed Method for the Synthesis of Carbazoles via Tandem C-H Functionalization and C-N Bond Formation” J. Org. Chem. 2008, 73, 7603-7610.

10. Handa, M.; Scheidt, K.; Bossart, M.; Zheng, N.; Roush, W. R. “Studies on the Synthesis of Apoptolidin A. 1. Synthesis of the C(1)-C(11) Fragment” J. Org. Chem. 2008, 73, 1031-1035.

9. Zheng, N.; Buchwald, S. L. “A Copper-Catalyzed Regiospecific Synthesis of N-Alkyl Benzimidazoles.” Org. Lett. 2007, 9, 4749-4751.

8. Zheng, N.; Anderson, K. W.; Huang, X.; Nguyen, H. N.; Buchwald, S. L. “A Palladium-Catalyzed Regiospecific Synthesis of N-Aryl Benzimidazoles.” Angew. Chem., Int. Ed. 2007, 46, 7509-7512.

7. Tsang, W. C. P.; Zheng, N.; Buchwald, S. L. “Combined C-H Functionalization/C-N Bond Formation Route to Carbazoles.” J. Am. Chem. Soc. 2005, 127, 14560-14561.

6. Zheng, N.; Armstrong, J. D., III; Keller, J.; Liu, T.; Purick, J. L.; Bhupathy, M.; Volante, R. P. “A Convergent Asymmetric Synthesis of the Growth Hormone Secretagogue.” Tetrahedron: Asymmetry 2003, 14, 3435-3446.

5. McWilliams, J. C.; Fleitz, F. J.; Zheng, N.; Armstrong, J. D., III “Preparation of N-Butyl 4-Chlorophenyl Sulfide.” Organic Syntheses 2002, 79, 43-51.

4. Fleitz, F. J.; Lyle, T. A.; Zheng, N.; Armstrong, J. D., III; Volante, R. P. “Kilogram Scale Synthesis of the Pyrazinone Acetic Acid Core of an Orally Efficacious Thrombin Inhibitor.” Synth. Commun. 2000, 30, 3171-3180.

3. Zheng, N.; McWilliams, J. C.; Fleitz, F. J.; Armstrong, J. D., III; Volante, R. P “Palladium-Catalyzed Synthesis of Aryl Sulfides from Aryl Triflates.” J. Org. Chem. 1998, 63, 9606-9607.

2. Zheng, N.; Armstrong, J. D., III; McWilliams, J. C.; Fleitz, F. J.; Volante, R. P “Aymmetric Synthesis of α–Amino Acid Derivatives via an Electrophilic Amination of Chiral Amide Cuprates with Li-t-Butyl-N-Tosyloxycarbamate.” Tetrahedron Lett. 1997, 38, 2817-2820.

1. McWilliams, J. C.; Armstrong, J. D., III; Zheng, N.; Bhupathy, M.; Volante, R. P.; Reider, P. “Tandem Asymmetric Transformations: an Asymmetric 1,2-Migration from a Higher Order Zincate Coupled with a Stereoselective Homoaldol Reaction.” J. Am. Chem. Soc. 1996, 118, 11970-11971.

2/1/2010
Our website is up.



Graduate student positions available
Perspective graduate students interested in joining the group are encouraged to contact Professor Zheng at the email address below nzheng@uark.edu.
The information about how to apply to our graduate program can be found here.

Group meeting are held at The Harrison Hale Lounge from 12 to 2 pm on Friday.

Zheng group Job Schedule 2010 Spring (PDF/36K)
Zheng Group meeting Schedule 2010 Spring (PDF/48K)

Group Outing Photos

        

Lab Tour Photos

        

        

        

     

Alumni Photos

CHEM 3613, Organic Chemistry II, Spring 2010

Download syllabus (PDF/112K)

Lecture 3 hours per week. Primarily for non-majors and B.A.
chemistry majors who do not take the CHEM 3703/3702L and 3713/3712L sequence.

Pre- or Corequisite: CHEM 3611L.
Corequisite: Drill component.
Prerequisite: CHEM 1123 and CHEM 1121L and CHEM 3603 and CHEM 3601L

Nan Zheng

Office: CHEM 211
Office Phone: 479-575-5078
Lab Phone: 479-575-2609
FAX: 479-575-4049
Email: nzheng@uark.edu