Citation: Li Shangfeng, Ma Xiuguang. Research Progress in the Synthesis of Homocamptothecin[J]. Chemistry, ;2018, 81(3): 203-208. shu

Research Progress in the Synthesis of Homocamptothecin

Sundia MediTech Co., Ltd., Shanghai 201203

Received Date: 17 May 2017
Accepted Date: 29 August 2017

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To date, there have been two ways to synthesize homocamptothecin including semi-synthesis and total synthesis. The former is simple and concise, yet with few substituent groups. It only produces the racemic homocamptothecin. On the contrary, the latter can introduce various substituent groups on ring A and B. This protocol can bring the asymmetric synthesis into practice, though the route seems a little lengthy. All the study advance of homocamptothecin at home and abroad was reviewed. Each group's synthetic protocol was introduced in depth along with their research results. The outlook of homocamptothecin in the field of medicine was foreshown, with the indication of the future research direction.
- Homocamptothecin,
- Topoisomerase I
1. [1]
  N H Oberlies, D J Kroll. J. Nat. Prod., 2004, 67:129~135.
2. [2]
  M E Wall, M C Wani, C E Cook et al. J. Am. Chem. Soc., 1966, 88:3888~3889.
3. [3]
  K Mross, H Richly, N Schleucher et al. Ann. Oncol., 2004, 15:1284~1294.
4. [4]
  O Lavergne, L L-Ginot, F P Rodas et al. J. Med. Chem., 1998, 41:5410~5419.
5. [5]
  X Wu, X Sun, Z Guo et al. J. Am. Chem. Soc. 2014, 136:3579~3588.
6. [6]
  M Ye, X Wang, J Tang et al. Chem. Sci., 2016, 7:4958~4965.
7. [7]
8. [8]
  Y Q Zhang, H J Zhang, J Zhang et al. Aust. J. Chem., 2011, 64:1547~1553.
9. [9]
  H F Hausheer, H Kochat, P Seetharamulu et al. WO: 9835940A1, 1998.
10. [10]
  A E Gabarda, W Du, T Isarno et al. Tetrahedron, 2002, 58:6329~6341.
11. [11]
  O Lavergne, L L Ginot, F P Rodas et al. Bioorg. Med. Chem. Lett., 1997, 7:2235~2238.
12. [12]
  C Bailly, A Lansiaux, L Dassonneville et al. Biochemistry, 1999, 38:15556~15563.
13. [13]
  D Demarquay, M Huchet, H Coulomb et al. Bioorg. Med. Chem. Lett., 1999, 9:2599~2602.
14. [14]
  D Demarquay, M Huchet, H Coulomb. Anti Cancer Drugs, 2001, 12:9~19.
15. [15]
  Z Mi, T G Burke. Biochemistry, 1994, 34:10325~10336.
16. [16]
17. [17]
  L Zhu, P Cheng, N Lei et al. Arch. Pharm. Chem. Life Sci. 2011, 344:726~734.
18. [18]
19. [19]
  D Z Li, C Y Wang, R H Liu et al. J. Asian Nat. Prod. Res., 2013, 15(11):1179~1188.
20. [20]
  D Bom, D P Curran, A J Chavan et al. J. Med. Chem., 1999, 42:3018~3022.
21. [21]
  D P Curran, W Du. Org. Lett., 2012, 4:3215~3218.
22. [22]
  M C Wani, P E Ronman, J T Lindley et al. J. Med. Chem. 1980, 23:554~560.
23. [23]
  Z Miao, C Sheng, W Zhang et al. Bioorg. Med. Chem., 2008, 16:1493~1510.
24. [24]
25. [25]
26. [26]
  Z Miao, J Zhang, L You et al. Bioorg. Med. Chem., 2010, 18:3140~3146.
27. [27]
  W Guo, W Liu, L Zhu et al. Chem. Biodiversity, 2011, 8(8):1539~1549.
28. [28]
  W Liu, L Zhu, W Guo et al. Eur. J. Med. Chem., 2011, 46:2408~2414.
29. [29]
  D Bigg, O Lavergne, F P Rodas et al. USP: 6339091 B1, 2002.
30. [30]
  O Lavergne, D Demarquay, C Bailly et al. J. Med. Chem., 2000, 43:2285~2289.
31. [31]
  R Peters, M Althaus, C Diolez et al. J. Org. Chem., 2006, 71:7583~7595.
32. [32]
  Y Luo, S Yu, L Tong et al. Eur. J. Med. Chem., 2012, 54:281~286.
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沈阳化工大学材料科学与工程学院沈阳 110142