Citation: Anquan Zheng, Tingting Zhou, Sasa Wang, Wenge Zhang, Xiuxiang Lu, Huiyu Chen, Haibo Tan. Total syntheses of hyperaspidinols A and B enabled by a bioinspired diastereoselective cascade sequence[J]. Chinese Chemical Letters, ;2022, 33(2): 885-889. doi: 10.1016/j.cclet.2021.08.035 shu

Total syntheses of hyperaspidinols A and B enabled by a bioinspired diastereoselective cascade sequence

Anquan Zheng ^{a, b, 1} ,
Tingting Zhou ^{a, b, 1} ,
Sasa Wang ^c ,
Wenge Zhang ^{a, d} ,
Xiuxiang Lu ^{a, d} ,
Huiyu Chen ^{b, *,} ,
Haibo Tan ^{a, *,}

a.
Key Laboratory of Plant Resources Conservation and Sustainable Utilization, Key Laboratory of South China Agricultural Plant Molecular Analysis, Guangdong Provincial Key Laboratory of Applied Botany, South China Botanical Garden, Chinese Academy of Sciences, Guangzhou 510650, China
b.
School of Pharmacy and Bioengineering, Chongqing University of Technology, Chongqing 400054, China
c.
Guangxi Key Laboratory of Chemistry and Engineering of Forest Products, Guangxi University for Nationalities, Nanning 530006, China
d.
University of Chinese Academy of Sciences, Beijing 100049, China

chenhuiyu@sit.edu.cn

tanhaibo@scbg.ac.cn

Received Date: 14 June 2021
Revised Date: 8 August 2021
Accepted Date: 8 August 2021
Available Online: 12 August 2021

Figures(8)

A bioinspired acid-triggered hemiacetalization/dehydration/[3 + 3]-type cycloaddition cascade process was disclosed, diastereoselectively furnishing furo[2,3-b]chromene skeleton under mild conditions. The viability of this approach was demonstrated by syntheses of a series of furo[2,3-b]chromene and pyrano[2,3-b]chromene derivatives. The successful total syntheses of two lignan-phloroglucinol hybrids, hyperaspidinols A and B, exemplified the synthetic utility of our biomimetic methodology.
- Total synthesis,
- Bioinspried,
- Diastereoselective,
- Cascade reaction,
- Hyperaspidinol
1. [1]
  Y.C. Lin, X.Y. Wu, S. Feng, et al., J. Org. Chem. 66(2001) 6252-6256. doi: 10.1021/jo015522r
2. [2]
  X.Y. Wu, X.H. Liu, Y.C. Lin, et al., Eur. J. Org. Chem. 71(2005) 4061-4064. doi: 10.1002/ejoc.200500326
3. [3]
  J.D. Pettigrew, P.D. Wilson, Org. Lett. 8(2006) 1427-1429. doi: 10.1021/ol060266w
4. [4]
  Z. Xu, Y. Li, Q. Xiang, et al., J. Med. Chem. 53(2010) 4642-4653. doi: 10.1021/jm1001502
5. [5]
  L. Feng, M.M. Maddox, M.Z. Alam, et al., J. Med. Chem. 57(2014) 8398-8420. doi: 10.1021/jm500853v
6. [6]
  C. Airoldi, F. Cardona, E. Sironi, et al., Chem. Commun. 47(2011) 10266-10268. doi: 10.1039/c1cc13046c
7. [7]
  Y. Luan, H. Sun, S.E. Schaus, Org. Lett. 13(2011) 6480-6483. doi: 10.1021/ol202772k
8. [8]
  X.J. Lv, W.W. Zhao, Y.H. Chen, et al., Org. Chem. Front. 6(2019) 1972-1976. doi: 10.1039/C9QO00366E
9. [9]
  Y.T. Lai, K. Nagaraju, R. Gurubrahamam, et al., Adv. Synth. Catal. 362(2020) 3846-3850. doi: 10.1002/adsc.202000667
10. [10]
  R. Rodriguez, R.M. Adlington, J.E. Moses, et al., Org. Lett. 6(2004) 3617-3619. doi: 10.1021/ol048479d
11. [11]
  J.S. Yadav, B.V.S. Reddy, P.N. Reddy, Chem. Lett. 33(2004) 1436-1437. doi: 10.1246/cl.2004.1436
12. [12]
  W. Luo, Q.S. Yu, M. Zhan, et al., J. Med. Chem. 48(2005) 986-994. doi: 10.1021/jm049309+
13. [13]
  B. Biswas, D. Sarkar, R.V. Venkateswaran, Tetrahedron 64(2008) 3212-3216. doi: 10.1016/j.tet.2008.01.097
14. [14]
  D.L. Paterson, D. Barker, Beilstein J. Org. Chem. 11(2015) 265-270. doi: 10.3762/bjoc.11.29
15. [15]
  J. Yang, G. Qiu, J. Jiang, et al., Adv. Synth. Catal. 359(2017) 2184-2190. doi: 10.1002/adsc.201601335
16. [16]
  J. Guo, H. Miao, Y. Zhao, et al., Chem. Commun. 55(2019) 5207-5210. doi: 10.1039/C9CC02170A
17. [17]
  L. Zhou, W.G. Yan, X.L. Sun, et al., Angew. Chem. Int. Ed. 59(2020) 18964-18969. doi: 10.1002/anie.202007068
18. [18]
  J. Wandji, S.S. Awanchiri, Z.T. Fomum, et al., Phytochemistry 38(1995) 1309-1313. doi: 10.1016/0031-9422(94)00671-F
19. [19]
  K. Krohn, M. Riaz, Tetrahedron Lett. 45(2004) 293-294. doi: 10.1016/j.tetlet.2003.10.189
20. [20]
  J.D. Pettigrew, P.D. Wilson, J. Org. Chem. 71(2006) 1620-1625. doi: 10.1021/jo052371+
21. [21]
  B. Panda, T.K. Sarkar, J. Org. Chem. 78(2013) 2413-2421. doi: 10.1021/jo302545n
22. [22]
  B. Roy, N. Rout, P. Kuila, et al., J Heterocyclic Chem. 58(2021) 8-27. doi: 10.1002/jhet.4152
23. [23]
  W. Wang, Y.H. Zeng, K. Osman, et al., J. Nat. Prod. 73(2010) 1815-1820. doi: 10.1021/np1004483
24. [24]
  S. Gibbons, B. Ohlendorf, I. Johnsen, Fitoterapia 73(2002) 300-304. doi: 10.1016/S0367-326X(02)00082-5
25. [25]
  X. Jia, Y. Wu, C. Lei, et al., Chin. Chem. Lett. 31(2020) 1263-1266. doi: 10.1016/j.cclet.2019.10.014
26. [26]
  Y. Ye, N. Jiang, X. Yang, et al., Chin. Chem. Lett. 31(2020) 2433-2436. doi: 10.1016/j.cclet.2020.04.028
27. [27]
  J. Ma, G. Xia, Y. Zang, et al., Chin. Chem. Lett. 32(2021) 1173-1176. doi: 10.1016/j.cclet.2020.07.037
28. [28]
  B. Zhen, X. Suo, J. Dang, et al., Chin. Chem. Lett. 32(2021) 2338-2341. doi: 10.1016/j.cclet.2020.10.027
29. [29]
  N. Duhamel, C.E. Rye, D. Barker, Asian J. Org. Chem. 2(2013) 491-493. doi: 10.1002/ajoc.201300086
30. [30]
  M.C. Sapu, J. Deska, Org. Biomol. Chem. 11(2013) 1376-1382. doi: 10.1039/c2ob27073k
31. [31]
  W.D. Liang, X.P. Cai, M.J. Dai, Chem. Sci. 12(2012) 1311-1316.
32. [32]
  V.T. Vu, X.L. Chen, L.Y. Kong, et al., Org. Lett. 22(2020) 1380-1384. doi: 10.1021/acs.orglett.9b04680
33. [33]
  V.T. Vu, M.T. Nguyen, W. Wang, et al., Org. Biomol. Chem. 18(2020) 6607-6611. doi: 10.1039/D0OB01412E
34. [34]
  H. Tan, H. Liu, X. Chen, et al., Org. Lett. 17(2015) 4050-4053. doi: 10.1021/acs.orglett.5b01970
35. [35]
  H. Liu, L. Huo, B. Yang, et al., J. Org. Lett. 19(2017) 4786-4789. doi: 10.1021/acs.orglett.7b02159
36. [36]
  H. Liu, W. Yu, X. Guo, et al., Org. Lett. 20(2018) 546-549. doi: 10.1021/acs.orglett.7b03630
37. [37]
  L. Huo, C. Dong, M. Wang, et al., Org. Lett. 22(2020) 934-938. doi: 10.1021/acs.orglett.9b04486
38. [38]
  X. Zhang, C. Dong, G. Wu, et al., Org. Lett. 22(2020) 8007-8011. doi: 10.1021/acs.orglett.0c02943
39. [39]
  D.H. Dethe, A.K. Nirpal, Org. Biomol. Chem. 17(2019) 7507-7516. doi: 10.1039/C9OB01426H
40. [40]
  A.J. Grenning, J.H. Boyce, J.A. Porco Jr, J. Am. Chem. Soc. 136(2014) 11799-11804. doi: 10.1021/ja5060302
41. [41]
  E. Jung, N. Dittrich, L.I. Pilkington, et al., Tetrahedron 71(2015) 9439-9456. doi: 10.1016/j.tet.2015.10.050
42. [42]
  O. Celaj, A.G. Durán, P. Cennamo, et al., Phytochem. Rev. 20(2021) 259-299. doi: 10.1007/s11101-020-09697-2
43. [43]
  D.S. Reddy, M. Kongot, A. Kumar, Tuberculosis 127(2021) 102050. doi: 10.1016/j.tube.2020.102050
44. [44]
  Z. Xu, Q.T. Chen, Y. Zhang, et al., Fitoterapia 150(2021) 104863. doi: 10.1016/j.fitote.2021.104863
45. [45]
  G.P. McGlacken, I.J.S. Fairlam, Nat. Prod. Rep. 22(2005) 369-385. doi: 10.1039/b416651p
46. [46]
  H.X. Liu, Y.C. Chen, Y. Liu, et al., Fitoterapia 114(2016) 40-44. doi: 10.1016/j.fitote.2016.08.010
47. [47]
  V. Brezáni1, V. Leláková, S. Hassan, et al., Viruses 10(2018) 360. doi: 10.3390/v10070360
48. [48]
  S. Prévost, K. Thai, N. Schützenmeister, et al., Org. Lett. 17(2015) 504-507. doi: 10.1021/ol503520f
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