Citation: Qiang Zhang, Jingxiang Pang, Tian-Zhang Wang, Feng Chen, Minghao Shen, Tianyu Li, Yongshuai Chai, Yu-Feng Liang, Jie Sun, Zhushuang Bai. Organocatalytic enantioselective construction of bicyclic γ-butrolactones[J]. Chinese Chemical Letters, ;2023, 34(7): 108121. doi: 10.1016/j.cclet.2022.108121 shu

Organocatalytic enantioselective construction of bicyclic γ-butrolactones

Qiang Zhang ^{a, 1} ,
Jingxiang Pang ^{a, 1} ,
Tian-Zhang Wang ^b ,
Feng Chen ^a ,
Minghao Shen ^a ,
Tianyu Li ^a ,
Yongshuai Chai ^a ,
Yu-Feng Liang ^{b, *,} ,
Jie Sun ^{a, *,} ,
Zhushuang Bai ^{a, *,}

a.
School of Pharmacy and Pharmaceutical Science & Institute of Materia Medica, Shandong First Medical University & Shandong Academy of Medical Sciences, NHC Key Laboratory of biotechnology drug (Shandong Academy of Medical Sciences), Key Lab for Rare & Uncommon Diseases of Shandong Province, Ji'nan 250117, China
b.
School of Chemistry and Chemical Engineering, Shandong University, Ji'nan 250100, China

yfliang@sdu.edu.cn

sunjie310@126.com

baizhushuang@163.com

Received Date: 9 October 2022
Revised Date: 23 December 2022
Accepted Date: 27 December 2022
Available Online: 29 December 2022

Figures(6)

An enantioselective organo-catalyzed reaction of furanones with α, β-unsaturated ketones has been established herein, which provides an efficient access to chiral bicyclic γ-butyrolactones in good yields, enantioselectivities and diastereoselectivities. Further transformations of product are demonstrated. A diamine mediated catalytic cycle is proposed.
- Organocatalyst,
- Asymmetric synthesis,
- Bicyclic γ-butyrolactone,
- Diamine,
- Cyclization
1. [1]
  M.E. Abbasov, R. Alvarino, C.M. Chaheine, et al., Nat. Chem. 11 (2019) 342–350. doi: 10.1038/s41557-019-0230-0
2. [2]
  K.S. McClymont, F.Y. Wang, A. Minakar, et al., J. Am. Chem. Soc. 142 (2020) 8608–8613. doi: 10.1021/jacs.0c03202
3. [3]
  Y. Nassar, O. Piva, Org. Biomol. Chem. 18 (2020) 5811–5815. doi: 10.1039/d0ob01169j
4. [4]
  J. Tong, T. Xia, B. Wang, Org. Lett. 22 (2020) 2730–2734. doi: 10.1021/acs.orglett.0c00689
5. [5]
  M.E. Rateb, W.E. Houssen, M. Schumacher, et al., J. Nat. Prod. 72 (2009) 1471–1476. doi: 10.1021/np900233c
6. [6]
  J.Q. Xiao, M.X. Gao, Z. Sun, et al., Eur. J. Med. Chem. 208 (2020) 112830. doi: 10.1016/j.ejmech.2020.112830
7. [7]
  X. Yu, Z.P. Che, H. Xu, Chem. Eur. J. 23 (2017) 4467–4526. doi: 10.1002/chem.201602472
8. [8]
  H.Y. Fan, Z.L. Zhu, H.C. Xian, et al., Front. Cell. Dev. Biol. 9 (2021) 709075. doi: 10.3389/fcell.2021.709075
9. [9]
  A. Kamal, S.M. Hussaini, A. Rahim, et al., Expert Opin. Ther. Pat. 25 (2015) 1025–1034. doi: 10.1517/13543776.2015.1051727
10. [10]
  Y.Q. Liu, J. Tian, K. Qian, et al., Med. Res. Rev. 35 (2015) 1–62. doi: 10.1002/med.21319
11. [11]
  A. Kumari, D. Singh, S. Kumar, Crit. Rev. Biotechnol. 37 (2017) 739–753. doi: 10.1080/07388551.2016.1228597
12. [12]
  M.V. Chelliah, S. Chackalamannil, Y. Xia, et al., J. Med. Chem. 50 (2007) 5147–5160. doi: 10.1021/jm070704k
13. [13]
  V.L. Serebruany, M.H. Kim, S.D. Fortmann, et al., Expert. Rev. Neurother. 15 (2015) 1377–1382. doi: 10.1586/14737175.2015.1111761
14. [14]
  P. Tricoci, Z. Huang, C. Held, et al., N. Engl. J. Med. 366 (2012) 20–33. doi: 10.1056/NEJMoa1109719
15. [15]
  D.A. Morrow, E. Braunwald, M.P. Bonaca, et al., N. Engl. J. Med. 15 (2012) 1404–1413. doi: 10.1056/NEJMoa1200933
16. [16]
  L. Yang, L.R. Qiao, C.X. Ji, et al., J. Nat. Prod. 76 (2013) 216–222. doi: 10.1021/np3006925
17. [17]
  L. Mayola, V. Piccialli, D. Sica, Tetrahedron Lett. 26 (1985) 1357–1360. doi: 10.1016/S0040-4039(00)94893-7
18. [18]
  M. Leiros, E. Alonso, M.E. Rateb, et al., Neuropharmacology 93 (2015) 285–93. doi: 10.1016/j.neuropharm.2015.02.015
19. [19]
  S. Gegunde, A. Alfonso, E. Alonso, et al., Cell. Mol. Neurobiol. 40 (2020) 603–615. doi: 10.1007/s10571-019-00758-5
20. [20]
  R.J. Shi, H.Y. Fan, X.H. Yu, et al., Biochem. Pharmacol. 200 (2022) 115039. doi: 10.1016/j.bcp.2022.115039
21. [21]
  Y. Gao, K. Han, Q. Wang, et al., Mol. Med. Rep. 17 (2018) 6506–6514.
22. [22]
  M. Gordaliza, P.A. Garcia, J.M. del Corral, et al., Toxicon 44 (2004) 441–459. doi: 10.1016/j.toxicon.2004.05.008
23. [23]
  I.A. Najar, R.K. Johri, J. Biosci. 39 (2014) 139–144. doi: 10.1007/s12038-013-9399-3
24. [24]
  S. Ezoe, Int. J. Environ. Res. Public. Health. 9 (2012) 2444–2453. doi: 10.3390/ijerph9072444
25. [25]
  C.C. Wu, T.K. Li, L. Farh, et al., Science 333 (2011) 459–462. doi: 10.1126/science.1204117
26. [26]
  W. Lau, E.S. Sattely, Science 349 (2015) 1224–1228. doi: 10.1126/science.aac7202
27. [27]
  M. Yusenko, A. Jakobs, K.H. Klempnauer, Sci. Rep. 8 (2018) 13159. doi: 10.1038/s41598-018-31620-1
28. [28]
  J.J. Yan, J.X. Sun, Z.Y. Zeng, Inflammopharmacology 26 (2018) 395–402. doi: 10.1007/s10787-017-0388-2
29. [29]
  F. Mack, N. Schafer, S. Kebir, et al., Oncology 86 (2014) 369–372. doi: 10.1159/000360295
30. [30]
  W. Zhao, Y. Cong, H.M. Li, et al., Nat. Prod. Rep. 38 (2021) 470–488. doi: 10.1039/d0np00041h
31. [31]
  M. Kluska, K. Wozniak, Int. J. Mol. Sci. 22 (2021) 6602. doi: 10.3390/ijms22126602
32. [32]
  S.Y. Shen, Y.R. Tong, Y.F. Luo, et al., Nat. Prod. Rep. 39 (2022), 1856–1875. doi: 10.1039/d2np00028h
33. [33]
  J.E. Frampton, Drugs 75 (2015) 797–808. doi: 10.1007/s40265-015-0387-9
34. [34]
  W. Liu, X. Fu, Y.F. Liu, et al., Mater. Sci. Eng. C 118 (2021) 111508. doi: 10.1016/j.msec.2020.111508
35. [35]
  R. Alvarino, E. Alonso, M.E. Abbasov, et al., ACS Chem. Neurosci. 10 (2019) 4102–4111. doi: 10.1021/acschemneuro.9b00329
36. [36]
  M. Alghazwi, Y.Q. Kan, W. Zhang, et al., J. Appl. Phycol. 28 (2016) 3599–3616. doi: 10.1007/s10811-016-0908-2
37. [37]
  E.M. Addo, H.B. Chai, A. Hymete, et al., J. Nat. Prod. 78 (2015) 827–835. doi: 10.1021/np501062f
38. [38]
  S. Hammami, Z. Li, M. Huang, et al., Nat. Prod. Res. 30 (2016) 2142–2148. doi: 10.1080/14786419.2016.1143828
39. [39]
  W. Kasel, P.G. Hultin, J.B. Jones, J. Chem. Soc., Chem. Commun. 17 (1986) 1563–1564.
40. [40]
  L. Huang, E. Romero, A.K. Ressmann, et al., Adv. Synth. Catal. 359 (2017) 2142–2148. doi: 10.1002/adsc.201700401
41. [41]
  Y.D. Tang, R.I.L. Meador, C.T. Malinchak, et al., J. Org. Chem. 85 (2020) 1823–1834. doi: 10.1021/acs.joc.9b01884
42. [42]
  E. Wada, A. Tyagi, A. Yamamoto, et al., Photochem. Photobiol. Sci. 16 (2017) 1744–1748. doi: 10.1039/c7pp00258k
43. [43]
  J. Moritani, Y. Hasegawa, Y. Kayaki, et al., Tetrahedron Lett. 55 (2014) 1188–1191. doi: 10.1016/j.tetlet.2013.12.103
44. [44]
  M.J. Schultz, S.S. Hamilton, D.R. Jensen, et al., J. Org. Chem. 70 (2005) 3343–3352. doi: 10.1021/jo0482211
45. [45]
  N. Kakiuchi, Y. Maeda, T. Nishimura, et al., J. Org. Chem. 66 (2001) 6620–6625. doi: 10.1021/jo010338r
46. [46]
  H. Shimizu, K. Nakata, T. Katsuki, Chem. Lett. 2002 (2002) 1080–1081.
47. [47]
  H. Shimizu, S. Onitsuka, H. Egami, et al., J. Am. Chem. Soc. 127 (2005) 5396–5413. doi: 10.1021/ja047608i
48. [48]
  T. OSAa, Y. Kashiwagi, T. ONO, et al., Int. J. Mater. Eng, Resour. 20 (2014) 49–53. doi: 10.5188/ijsmer.20.49
49. [49]
  H. Tanaka, Y. Kawakami, K. Goto, et al., Tetrahedron Lett. 42 (2001) 445–448. doi: 10.1016/S0040-4039(00)01979-1
50. [50]
  S.M. Xu, Z. Wang, X.M. Zhang, et al., Eur. J. Org. Chem. 2011 (2011) 110–116. doi: 10.1002/ejoc.201001130
51. [51]
  M.D. Mihovilovic, P. Kapitán, Tetrahedron Lett. 45 (2004) 2751–2754. doi: 10.1016/j.tetlet.2004.02.036
52. [52]
  M.D. Mihovilovic, P. Kapitan, P. Kapitanova, ChemSusChem 1 (2008) 143–148. doi: 10.1002/cssc.200700069
53. [53]
  F. Rudroff, M.J. Fink, R. Pydi, et al., Monatsh. Chem. 148 (2017) 157–165. doi: 10.1007/s00706-016-1873-9
54. [54]
  T.G. Chen, L.M. Barton, Y.T. Lin, et al., Nature 560 (2018) 350–354. doi: 10.1038/s41586-018-0391-9
55. [55]
  P. Cao, X.M. Zhang, J. Am. Chem. Soc. 121 (1999) 7708–7709. doi: 10.1021/ja991547k
56. [56]
  C. Schur, H. Kelm, T. Gottwald, et al., Org. Biomol. Chem. 12 (2014) 8288–8307. doi: 10.1039/C4OB01266F
57. [57]
  Y. Xu, T.Y. Zhai, Z. Xu, et al., Trends Chem. 4 (2022) 191–205. doi: 10.1016/j.trechm.2021.12.010
58. [58]
  F. Vetica, P. Chauhan, S. Dochain, et al., Chem. Soc. Rev. 46 (2017) 1661–1674. doi: 10.1039/C6CS00757K
59. [59]
  F. Giacalone, M. Gruttadauria, P. Agrigento, et al., Chem. Soc. Rev. 41 (2012) 2406–2447. doi: 10.1039/C1CS15206H
60. [60]
  B. Han, X.H. He, Y.Q. Liu, et al., Chem. Soc. Rev. 50 (2021) 1522–1586. doi: 10.1039/d0cs00196a
61. [61]
  Y.B. Wang, B. Tan, Acc. Chem. Res. 51 (2018) 534–547. doi: 10.1021/acs.accounts.7b00602
62. [62]
  W.N. Ottou, H. Sardon, D. Mecerreyes, et al., Science 56 (2016) 64–115.
63. [63]
  Y. Qin, L. Zhu, S. Luo, Chem. Rev. 117 (2016) 9433–9520.
64. [64]
  K. Zhao, Y. Zhi, T. Shu, et al., Angew. Chem. Int. Ed. 55 (2016) 12104–12108. doi: 10.1002/anie.201606947
65. [65]
  W. Wu, X. Yuan, J. Hu, et al., Org. Lett. 15 (2013) 4524–4527. doi: 10.1021/ol4020865
66. [66]
  S. Huang, H. Wen, Y. Tian, et al., Angew. Chem. Int. Ed. 60 (2021) 21486–21493. doi: 10.1002/anie.202108040
67. [67]
  H. Hu, C. Meng, Y. Dong, et al., ACS Catal. 5 (2015) 3700–3703. doi: 10.1021/acscatal.5b00680
68. [68]
  X. Gu, T. Guo, Y. Dai, et al., Angew. Chem. Int. Ed. 54 (2015) 10249–10253. doi: 10.1002/anie.201504276
69. [69]
  W. Wang, J. Wang, S. Zhou, et al., Chem. Commun. 49 (2013) 1333–1335. doi: 10.1039/c2cc35488h
70. [70]
  L.D. Guo, X.Z. Huang, S.P. Luo, et al., Angew. Chem. Int. Ed. 55 (2016) 4064–4068. doi: 10.1002/anie.201512005
71. [71]
  X. Li, M. Lu, Y. Dong, et al., Nat. Commun. 5 (2014) 4479. doi: 10.1038/ncomms5479
72. [72]
  W. Wu, H. Huang, X. Yuan, et al., Chem. Commun. 48 (2012) 9180–9182. doi: 10.1039/c2cc34321e
73. [73]
  Y. Wei, S. Wen, Z. Liu, et al., Org. Lett. 17 (2015) 2732–2735. doi: 10.1021/acs.orglett.5b01149
74. [74]
  M. Shi, Q. Zhang, J. Gao, et al., Angew. Chem. Int. Ed. 2022, e202209044.
75. [75]
  C. Portolani, G. Centonze, S. Luciani, et al., Angew. Chem. Int. Ed. 2022 (61) e202209895.
76. [76]
  T.L. Liu, C.J. Wang, X. Zhang, Angew. Chem. Int. Ed. 52 (2013) 8416–84199. doi: 10.1002/anie.201302943
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