Research Interests
Natural products have long been a rich source for the discovery of novel therapeutic agents as exemplified by the successful cases of aspirin, penicillin, morphine, taxol, artemisinin and the statins. The structures of these naturally occurring molecules are rich in
sp3 carbons and stereogenic centers, and thus represent much broader chemical space than known drugs and libraries of drug-like molecules. Accordingly, the construction of natural products and derived chemical libraries might offer appealing opportunities to address drug targets by providing new pharmacophores and binding geometrics. Research in my laboratory focuses on bioactive natural products, which intend to serve as both the inspiration for the discovery of novel synthetic strategies and a chemical starting point for the discovery of novel therapeutics.
Selected Achievements
Our central theme is to utilize skeletal rearrangements as the key strategies for the total synthesis of bioactive natural products and the construction of natural product-like molecules for medicinal chemical research. In this context, we have developed a conceptually distinct strategy for the synthesis of the indoline/indolenine core of akuammiline natural products via an unprecedented aza-pinacol rearrangement. The applications of this strategy and related methods have resulted in the concise chemical synthesis of minfiensine, the first total synthesis of calophyline A, the first total synthesis of grandilodine B, the practical asymmetric total synthesis of goniomitine, and the unified total synthesis of deformylcorymine, strictamine and calophyline A.
Selected Publications
1. Unified Total Syntheses of Structurally Diverse Akuammiline Alkaloids. Xie, X.; Wei, B.; Li, G.;
Zu, L.*
Org. Lett.
2017,
19, 5430.
2. Catalytic Enantioselective Aza-pinacol Rearrangement. Yu, Y.; Li, J.; Jiang, L.; Zhang, J.-R.;* Zu, L.* Angew. Chem. Int. Ed. 2017, 56, 9217.
3. Total synthesis of (±)-Grandilodine B. Wang, C.; Wang, Z.; Xie, X.; Yao, X.; Li, G.; Zu, L.* Org. Lett. 2017, 19, 1828.
4. Bio-Inspired Fragmentations: Rapid Assembly of Indolones, 2-Quinolinones, and (-)-Goniomitine. Li, H.; Cheng, P.; Jiang, L.; Yang, J.; Zu, L.* Angew. Chem. Int. Ed. 2017, 56, 2754.
5. Total Synthesis of Calophyline A. Li, G.; Xie, X.; Zu, L.* Angew. Chem. Int. Ed. 2016, 55, 10483. This paper was selected as the back cover: Angew. Chem. Int. Ed. 2016, 55, 10524.
6. Divergent Synthesis of Hydro-g-Carbolines and Multisubstituted Indoles through Grob Fragmentation/Mannich Cyclization. Jiang, L.; Yu, Y.; Li, G.; Zu, L.* Chem. Asian J. 2016, 11, 2838.
7. The Development of Aza-Pinacol and Aza-Semipinacol Rearrangements for the Synthesis of Nitrogen-Containing Molecules. Yu, Y.; Li, G.; Zu, L.* Synlett. 2016, 27, 1303. (invited Synpacts)
8. An Indoxyl-Based Strategy for the Synthesis of Indolines and Indolenines. Yu, Y.; Li, G.; Jiang, L.; Zu, L.* Angew. Chem. Int. Ed. 2015, 54, 12627.
9. tert-Butyl Hypochlorite Mediated Diastereoselective Oxidative Coupling: Access to 1- Functionalized Tetrahydrocarbazoles. Jiang, L.; Xie, X.; Zu, L.* RSC Adv. 2015, 5, 9204.
10. Rapid Assembly of Functionalized Hydrodibenzofurans via Semipinacol Rearrangements. Yao, X.; Xie, X.; Wang, C.; Zu, L.* Org. Lett. 2015, 17, 4356.
11. [3 + 2] Annulations between Indoles and a, b-Unsaturated ketones: Access to Pyrrolo[1,2-a] Indoles and Model Reactions toward the Originally Assigned Structure of Yuremamine. Li, H.; Wang, Z.; Zu, L.* RSC Adv. 2015, 5, 60962.
12. Efficient Assembly of Polysubstituted Pyrroles via a (3+2) Cycloaddition/Skeletal Rearrangement/Redox Isomerization Cascade Reaction. Yu, Y.; Wang, C.; He, X.; Yao, X.; Zu, L.* Org. Lett. 2014, 16, 3580.
