Citation: Qiu Bin, Xia Chungu, Sun Wei. Bioinspired manganese complexes catalyzed epoxidation for the synthesis of the epoxyketone fragment of carfilzomib[J]. Chinese Chemical Letters, ;2019, 30(3): 698-701. doi: 10.1016/j.cclet.2018.10.023 shu

Bioinspired manganese complexes catalyzed epoxidation for the synthesis of the epoxyketone fragment of carfilzomib

Qiu Bin ^a,b ,
Xia Chungu ^a ,
Sun Wei ^a,*,

a.
Key Laboratory for Oxo Synthesis and Selective Oxidation, Suzhou Research Institute of LICP, Lanzhou Institute of Chemical Physics (LICP), Chinese Academy of Sciences, Lanzhou 730000, China
b.
University of Chinese Academy of Sciences, Beijing 100049, China

wsun@licp.cas.cn

Received Date: 29 September 2018
Revised Date: 15 October 2018
Accepted Date: 22 October 2018
Available Online: 25 March 2018

Figures(6)

We report herein an efficient catalytic epoxidation reaction for the synthesis of epoxyketone (tert-butyl ((S)-4-methyl-1-((R)-2-methyloxiran-2-yl)-1-oxopentan-2-yl)carbamate), which is an important synthetic intermediate of carfilzomib. A series of bioinspired manganese complexes bearing N4 ligands are carefully investigated in the epoxidation of enone precursor with H₂O₂ as oxidant in the presence of carboxylic acid (e.g., acetic acid).
- Catalytic epoxidation,
- Bioinspired manganese complexes,
- Hydrogen peroxide,
- Epoxyketone,
- Carfilzomib
1. [1]
  K. Redic, J. Pharm. Pharmcol. 65 (2013) 1095-1106. doi: 10.1111/jphp.12072
2. [2]
  A. Rentsch, D. Landsberg, T. Brodmann, et al., Angew. Chem. Int. Ed. 52 (2013) 5450-5488. doi: 10.1002/anie.201207900
3. [3]
  K.B. Kim, C.M. Crews, Nat. Prod. Rep. 30 (2013) 600-604. doi: 10.1039/c3np20126k
4. [4]
  D.L. Hughes, Org. Process. Res. Dev. 20 (2016) 2028-2042. doi: 10.1021/acs.oprd.6b00374
5. [5]
  M.S. Smyth, G.J. Laidig, U.S. Patent, 8207297 B2, 2012.
6. [6]
  G.J. Laidig, P.A. Radel, M.S. Smyth, U.S. Patent, 0256324 A1, 2005.
7. [7]
  N. Sin, K.B. Kim, M. Elofsson, et al., Bioorg. Med. Chem. Lett. 9 (1999) 2283-2288. doi: 10.1016/S0960-894X(99)00376-5
8. [8]
  M.S. Smyth, G.J. Laidig, U.S. Patent, 0094930 A1, 2012.
9. [9]
  P. Phiasivongsa, L.C. Sehl, W.D. Fuller, G.J. Laidig, U.S. Patent, 8921583 B2, 2014.
10. [10]
  B. Zheng, Q. Gao, X. Zhang, B. Ding, X. Yang, CN Patent, 104230857 A, 2014.
11. [11]
  X.L. Ni, J. Liu, Y.Y. Liu, et al., Chin. Chem. Lett. 28 (2017) 1057-1061. doi: 10.1016/j.cclet.2017.01.020
12. [12]
  S.C. Xu, S.J. Zhu, L.W. Bi, et al., Chin. Chem. Lett. 28 (2017) 575-578. doi: 10.1016/j.cclet.2016.11.020
13. [13]
  F. Wang, T.Q. Wei, P. Xu, et al., Chin. Chem. Lett. 30 (2019) 379-382. doi: 10.1016/j.cclet.2018.08.006
14. [14]
  C.X. Miao, C.G. Xia, W. Sun, Sci. Sin. Chim. 44 (2014) 1865-1875. doi: 10.1360/N032014-00199
15. [15]
  K.P. Bryliakov, E.P. Talsi, Coord. Chem. Rev. 276 (2014) 73-96. doi: 10.1016/j.ccr.2014.06.009
16. [16]
  A. Murphy, G. Dubois, T.D.P. Stack, J. Am. Chem. Soc. 125 (2003) 5250-5251. doi: 10.1021/ja029962r
17. [17]
  L. Gómez, I. Garcia-Bosch, A. Company, et al., Dalton Trans. 47 (2007) 5539-5545.
18. [18]
  M. Wu, B. Wang, S.F. Wang, et al., Org. Lett. 11 (2009) 3622-3625. doi: 10.1021/ol901400m
19. [19]
  R.V. Ottenbacher, K.P. Bryliakov, E.P. Talsi, Adv. Synth. Catal. 353 (2011) 885-889. doi: 10.1002/adsc.v353.6
20. [20]
  W. Dai, S.S. Shang, B. Chen, et al., J. Org. Chem. 79 (2014) 6688-6694. doi: 10.1021/jo501178k
21. [21]
  O.Y. Lyakin, R.V. Ottenbacher, K.P. Bryliakov, et al., ACS Catal. 2 (2012) 1196-1202. doi: 10.1021/cs300205n
22. [22]
  O. Cussó, I. Garcia-Bosch, X. Ribas, et al., J. Am. Chem. Soc.135 (2013) 14871-14878. doi: 10.1021/ja4078446
23. [23]
  C.X. Miao, B. Wang, Y. Wang, et al., J. Am. Chem. Soc. 138 (2016) 936-943. doi: 10.1021/jacs.5b11579
24. [24]
  B. Wang, C.X. Miao, S.F. Wang, et al., Chem. Eur. J. 18 (2012) 6750-6753. doi: 10.1002/chem.201103802
25. [25]
  J.Y. Du, C.X. Miao, C.G. Xia, et al., Chin. Chem. Lett. 29 (2018) 1869-1871. doi: 10.1016/j.cclet.2018.04.036
26. [26]
  D.Y. Shen, C.X. Miao, S.F. Wang, et al., Org. Lett. 16 (2014) 1108-1111. doi: 10.1021/ol4037083
27. [27]
  X.E. Wang, C.X. Miao, S.F. Wang, et al., ChemCatChem 5 (2013) 2489-2494. doi: 10.1002/cctc.201300102
28. [28]
  J.Y. Du, C.X. Miao, C.G. Xia, et al., ACS Catal. 8 (2018) 4528-4538. doi: 10.1021/acscatal.8b00874
29. [29]
  D.Y. Shen, C.X. Miao, S.F. Wang, et al., Eur. J. Inorg. Chem. (2014) 5777-5782.
30. [30]
  H. So, Y.J. Park, K.B. Cho, et al., J. Am. Chem. Soc. 136 (2014) 12229-12232. doi: 10.1021/ja506275q
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