Citation: Jingyuan He, Zekai Wang, Xianwei Qi, Kaiyuan Chen, Jiang Bian. Application and Prospect of Molecular Skeletal Editing in Drug Synthesis[J]. University Chemistry, ;2023, 38(10): 313-323. doi: 10.3866/PKU.DXHX202301033 shu

Application and Prospect of Molecular Skeletal Editing in Drug Synthesis

1.
College of Chemistry and Molecular Engineering, Peking University, Beijing 100871, China;
2.
School of Physics, Peking University, Beijing 100871, China

Corresponding author: Jiang Bian, bj@pku.edu.cn
Received Date: 26 January 2023
Revised Date: 8 May 2023

Molecular editing, including peripheral and skeletal editing, is an area of interest in the field of organic synthesis. Typically, the peripheral editing of C―H bonds is conventionally used for molecular editing. By contrast, skeletal editing is a novel method, which has broader applications in total synthesis and drug development, with advantages of easy operation, high specificity, and simple synthetical routes. This review introduces two skeletal editing examples using common reactions. By comparisons with conventional methods, the applications of molecular editing in drug synthesis are revealed. Moreover, this review predicts the future applications of molecular editing by presenting some state-of-the-art developments in this field.
- Molecular editing,
- Skeletal editing,
- Drug synthesis,
- Drug development
1. [1]
  Kennedy, S. H.; Dherange, B. D.; Berger, K. J.; Levin, M. D. Nature 2021, 593, 223.
2. [2]
  Dherange, B. D.; Kelly, P. Q.; Liles, J. P.; Sigman, M. S.; Levin, M. D. J. Am. Chem. Soc. 2021, 143, 11337.
3. [3]
  -499.
4. [4]
  Woo, J.; Christian, A. H.; Burgess, S. A.; Yuan, J.; Mansoor, U. F.; Levin, M. D. Science 2022, 376, 527.
5. [5]
  Reisenbauer, J. C.; Green, O.; Franchino, A.; Finkelstein, P.; Morandi, B. Science 2022, 377, 1104.
6. [6]
  Qin, H.; Cai, W.; Wang, S.; Guo, T.; Li, G.; Lu, H. Angew. Chem. Int. Ed. 2021, 60, 20678.
7. [7]
  Zippel, C.; Seibert, J.; Bräse, S. Angew. Chem. Int. Ed. 2021, 60, 19522.
8. [8]
  Lyu, H.; Kevlishvili, I.; Yu, X.; Liu, P.; Dong, G. Science 2021, 372, 175.
9. [9]
  Patel, S. C.; Burns, N. Z. J. Am. Chem. Soc. 2022, 144, 17797.
10. [10]
  Hui, C.; Antonchick, A. P. Bioorg. Med. Chem. 2022, 67, 116817.
11. [11]
  Ma, D.; Martin, B. S.; Gallagher, K. S.; Saito, T.; Dai, M. J. Am. Chem. Soc. 2021, 143, 16383.
12. [12]
  Yuan, P.; Gerlinger, C. K. G.; Herberger, J.; Gaich, T. J. Am. Chem. Soc. 2021, 143, 11934.
13. [13]
  Fu, C.; Zhang, Y.; Xuan, J.; Zhu, C.; Wang, B.; Ding, H. Org. Lett. 2014, 16, 3376.
14. [14]
  Fischer, D. F.; Sarpong, R. J. Am. Chem. Soc. 2010, 132, 5926.
15. [15]
16. [16]
  Kröhnk, F. Angew. Chem. Int. Ed. 1963, 2, 225.
17. [17]
  Yuan, C.; Chang, C.; Siegel, D. J. Org. Chem. 2013, 78, 5647.
18. [18]
  Yuan, C.; Chang, C.-T.; Axelrod, A.; Siegel, D. J. Am. Chem. Soc. 2010, 132, 5924.
19. [19]
  Nakamura, M.; Chi, Y.; Yan, W.; Yonezawa, A.; Nakasugi, Y.; Yoshizawa, T.; Hashimoto, F.; Kinjo, J.; Nohara, T.; Sakurada, S.Planta Med. 2001, 67, 114.
20. [20]
  Gutekunst, W. R.; Baran, P. S. J. Am. Chem. Soc. 2011, 133, 19076.
21. [21]
  Hu, J.; Feng, L.; Wang, L.; Xie, Z.; Tang, Y.; Li, X. J. Am. Chem. Soc. 2016, 138, 13151.
22. [22]
  Pachaly, B.; West, R. Angew. Chem. Int. Ed. 1984, 23, 454.
23. [23]
  Jurczyk, J.; Woo, J.; Kim, S. F.; Dherange, B. D.; Sarpong, R.; Levin, M. D. Nat. Synth. 2022, 1, 352.
24. [24]
  Golding, B. T. The Story of Rucaparib (Rubraca). In Successful Drug Discovery; Fischer, J., Klein, C., Childers, W. E., Eds.; Wiley-VCH:Weinheim, Germany, 2019; pp. 201-223.
25. [25]
  Fout, A. R.; Bailey, B. C.; Tomaszewski, J.; Mindiola, D. J. J. Am. Chem. Soc. 2007, 129, 12640.
26. [26]
  Morofuji, T.; Inagawa, K.; Kano, N. Org. Lett. 2021, 23, 6126.
27. [27]
  Holovach, S.; Melnykov, K. P.; Poroshyn, I.; Iminov, R. T.; Dudenko, D.; Kondratov, I.; Levin, M.; Grygorenko, O. O. Chem. Eur. J. 2023, 29, e202203470.
28. [28]
  Rostovtsev, V. V.; Green, L. G.; Fokin, V. V.; Sharpless, K. B. Angew. Chem. Int. Ed. 2002, 41, 2596.
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沈阳化工大学材料科学与工程学院沈阳 110142