Faculty | Yefeng TANG, Ph. D.

Yefeng TANG, PI

Tenure-Track Associate Professor, The Department of Pharmaceutical Chemistry and Engineering, School of Pharmaceutical Science, Tsinghua University; Joint Professor, Collaborative Innovation Center for Biotherapy, West China Medical School, Sichuan University Prof. Yefeng Tang obtained his B.S. from Lanzhou University in 1999 and M.S. from the Institute of Materia Medica, Chinese Academy of Medical Science in 2003. After that, he pursued his Ph.D. with Prof. Zhen Yang at Peking University (2003-2006). From 2006 to 2009, he worked as a research associate with Prof. K. C. Nicolaou in The Scripps Research Institute. In 2010, he started his independent career as a tenure-track assistant professor in the Department of Pharmacology and Pharmaceutical Sciences, Tsinghua University, and was promoted to an associate professor in 2014. He is also a joint professor of the collaborative innovation center for biotherapy, West China Medical School, Sichuan University. His research interests mainly focus on synthetic organic chemistry and medicinal chemistry. So far, he has published over 40 peer-reviewed papers on the leading journals such as J. Am. Chem. Soc., Angew. Chem. Int. Ed., Org. Lett. and Chem. Commun.

 

Research Interests

The world consists of various different molecules. While chemists like molecules for their novel structures, biologists are obsessed with their fascinating functions. Undoubtedly, bioactive molecules play a pivotal role to connect the chemistry, biology and medicinal chemistry. The major research interests in Tang's laboratory could be defined as “biological function-oriented chemical synthesis”. Simply speaking, the primary goal of their research is to discover and develop new reactions and strategies which enable the rapid access of biologically important molecules (either natural products or privileged heterocyclic compounds), and then apply them to the relevant biomedical studies. Currently, the major research areas in Tang's laboratory include but not limited to: (1) total synthesis of natural products which have unique molecular architecture, important biological profile and novel biosynthetic pathway; (2) development of new synthetic methods which enable the raid access of privileged structures in natural products and drugs; (3) design, synthesis and biological evaluation of small molecules as anti-viral agent (anti-HCV and anti-HBV) or antibiotics, and( 4) development new bioorthogonal reactions and their application in medicinal chemistry and chemical biology.

Scientific Contributions

Prof. Tang has been working in the field of organic synthetic chemistry and medicinal chemistry over the past decade. So far, he and his group has accomplished the total synthesis of over 30 complex natural products, examples of which include schindilactone A, sporolide B, rossinone B, merochlorins A-B, xanthanolides, stemoamide and periconiasins A-F. Particularly, the total synthesis of sporolide B was selected in “Classics in Total Synthesis III”, and the total synthesis of schindilactone A was published as the cover article of Angew. Chim. Int. Ed. By making these molecules, his group not only discovered various new chemistries that attracted broad interests from chemical community, but also paved the way to apply those natural products in related biomedical studies. His group has also succeeded in development of a number of novel synthetic methodologies which enable the rapid construction of various privileged structures of medicinal importance, such as the controllable dyotropic rearrangement of 3,4-cis-b-lactone, gold-carbenoid catalyzed 2,3-sigmatropic rearrangement and Rh(II)-azavinylcarbene-promoted cycloaddition reactions. Of note, some of these small molecule libraries have been successfully applied to the “fragment-based drug discovery” in a collaborative program between his group and Bayer Health Care Company Ltd.

Selected Achievements

1. Completed the collective total syntheses of several prominent families of natural products which have novel chemical structures and important biological activities, examples of which include xanthanolides, stemoamides and periconiasins A-G.

Figure 1:Selected natural products completed in Tang’s group 

2.Developed a number of novel and efficient synthetic methods which enable the rapid construction of various privileged structures of natural products and drugs, examples of which include dyotropic rearrangement of 3,4-cis-b-lactone, and the Rh(II)-azavinylcarbene-promoted cycloaddition reactions.

Figure 2:Rh-azavinylcarbene-promoted cycloaddition reactions

3. Discovered a new class of anti-HCV entry inhibitors which displayed potent activity (IC50 = 10-20 nM) and novel mechanism of action.

Figure 3: Development of novel anti-HCV virus entry inhibitor
 


 Selected Publications

1. Tian, C.; Lei, X. Q.; Wang, Y. H.; Dong, Z.; Liu, G.*Tang, Y. F.* Total Syntheses of Periconiasins A-E. Angew. Chem. Int. Ed. 201655, 6992–6996.
2.  Lei, X. Q.; L. B. Li; He, Y. P.*; Tang, Y. F.* Rhodium(II)-Catalyzed Formal [3+2] Cycloaddition of N-Sulfonyl-1,2,3-triazoles with Isoxazoles: Entry to Polysubstituted 3‑Aminopyrroles. Org. Lett. 201517, 5224–5227.
3.  Wang, H.; Wang, S.; Cheng, L. L.; Chen, L. G.; Wang, Y. G.; Qing, J.; Huang, S. D.; Wang, Y. H.; Lei, X. Q.; Wu, Y. F.; Ma, Z. L.; Zhang, L. Q.*; Tang, Y. F.* Discovery of Imidazo[1,2-a][1,8]naphthyridine Derivatives as Potential HCV Entry Inhibitor. ACS Med. Chem. Lett. 20156, 977−981.
4. Yang, H. Z.; Feng, J.; Li, Y. H.; Tang, Y. F.* Biomimetic Syntheses of Rubialatins A, B and Related Congeners. Org. Lett. 201517, 1441–1444.
5. Wang, Y. H.; Lei, X. Q.; Tang, Y. F.* Rh(II)-catalyzed Cycloadditions of 1-Tosyl 1,2,3-Triazoles with 2H-Azirines: Switchable Reactivity of Rh-azavinylcarbene as [2C]- or Aza-[3C]-Synthon. Chem. Commun. 2015, 51, 4507–4510.
6. Shang, H.; Liu, J. H.; Bao, R. Y.; Cao, Y. Zhao, K.; Xiao, C. Q.; Zhou, B.; Hu, L. H.*; Tang, Y. F.* Biomimetic Synthesis: Discovery of Xanthanolide Dimers. Angew. Chem. Int. Ed. 201453, 14494–14498.
7. Shang, H. Wang, Y. H. Tian, Y. Feng, J.; Tang, Y. F.* The Divergent Synthesis of Nitrogen Heterocycles by Rhodium(II)-Catalyzed Cycloadditions of 1-Sulfonyl 1,2,3-Triazoles with 1,3-Dienes. Angew. Chem. Int. Ed. 2014, 53, 5662–5666.
8. Fu, J. K.; Shang, H.; Wang, Z. F.; Chang, L.; Shao, W. B.; Yang, Z.*; Tang Y. F.* Gold-Catalyzed Rearrangement of Allylic Oxonium Ylides: Efficient Synthesis of Highly Functionalized Dihydrofuran-3-ones. Angew. Chem. Int. Ed. 201352, 4198–4202.
9. Yang H. Z.; Feng J.; Tang, Y. F.* Biomimetic Total Syntheses of Spirobacillenes A and B. Chem. Commun. 201349, 6442–6444.
10. Ren, W. W.; Bian, Y. C.; Zhang, Z. Y.; Shang, H.; Zhang, P. T.; Chen, Y. J.; Yang, Z.*; Luo T. P.*; Tang Y. F.* Enantioselective and Collective Syntheses of Xanthanolides by Controllable Dyotropic Rearrangement of cis-b-Lactones. Angew. Chem. Int. Ed. 201251, 6984–6988.
11. X. Qing, Ren W. W; Chen, Z. X.; Sun, T. W.; Li, Y.; Ye, Q. D.; Gong, J. X.; Meng, F. K.; You, L.; Liu, Y. F.; Zhao, M. Z.; Xu, L. M.; Shan, Z. H.; Shi, Y.; TangY. F.*; Chen, J. H.*; Yang Z.* Diastereoselective Total Synthesis of (+)-Schindilactone A. Angew. Chem. Int. Ed. 201150, 7373–7377.
12. Nicolaou, K. C.*; Wang, J. H.; Tang, Y. F.; Botta, L. Total Synthesis of Sporolide B and 9-epi-Sporolide B. J. Am. Chem. Soc. 2010132, 11350–11363.
13. Nicolaou, K. C.*; Tang, Y. F.; Wang, J. H. Total Synthesis of Sporolide B. Angew. Chem. Int. Ed. 200948, 3501–3505.
14. Nicolaou, K. C.*; Stephan, A. F; Lister, T.; Li, A.; Tria, G. S.; Turner, C. I.; Tang, Y. F.; Wang, J. H.; Denton, R. M.; Edmonds, D. J. Design, Synthesis, and Biological Evaluation of Platensimycin Analogues with Varying Degree of Molecular Complexity. J. Am. Chem. Soc. 2008130, 13110–13119.
15. Nicolaou, K. C.*; Wang, J. H.; Tang, Y. F. Synthesis of the Sporolide Ring Framework through A Cascade Sequence Involving An Intramolecular [4+2] Cycloaddition Reaction of an o-Quinone. Angew. Chem. Int. Ed. 200847, 1432–1435.
16. Nicolaou, K. C.*; Tang, Y. F.; Wang, J. H. Total Synthesis and Antibacterial Properties of Carbaplatensimycin. J. Am. Chem. Soc. 2007129, 14850–14851.
17. Nicolaou, K. C*.; Tang, Y. F.; Wang, J. H. Formal Synthesis of (+)-Platensimycin. Chem. Comm. 2007, 1922–1923.
18. Tang, Y. F.; Zhang, Y. D.; Dai, M. J.; Luo, T. P.; Deng, L. J.; Chen, J. H.*; Yang, Z.* A Highly Efficient Synthesis of the FGH Ring of Micrandilactone A. Application of Tioureas as Ligands in the Co-catalyzed Pauson-Khand Reaction and Pd-Catalyzed Carbonylative Annulation. Org. Lett. 20057, 885–888.
19. Tang, Y. F.; Deng, L. J.; Zhang, Y. D.; Dong, G. B.; Chen, J. H.*; Yang, Z.*. Thioureas as Ligands in the Pd-Catalyzed Intramolecular Pauson-Khand Reaction. Org. Lett. 20057, 1657–1659.
20.  Tang, Y. F.; Deng, L. J.; Zhang, Y. D.; Dong, G. B.; Chen, J. H.*; Yang, Z.* Tetramethyl Thiourea/Co2(CO)8-Catalyzed Pauson-Khand Reaction Under Balloon Pressure of CO. Org. Lett. 20057, 593–595.

Patent

1. Preparation of Amide Derivatives for Treatment of HCV. Tang, Y. F.; Zhang, L. Q.; Wang, Y. G.; Qing, J.; Huang, S. D. Faming Zhuanli Shenqing (2013), CN 103333168 A 20131002.