REVIEW

Recent Progresses in the Synthesis of Solanoeclepin A

  • Mao Sun ,
  • Fayang Qiu ,
  • Wei-Dong Li
Expand
  • a Pharmaceutical Laboratory, An Shun City People’s Hospital, Anshun 561000;
    b Chongqing Key Laboratory of Natural Product Synthesis and Drug Research, School of Pharmaceutical Sciences, Chongqing University, Chongqing 40133
    c School of Life Science and Engineering, Southwest Jiaotong University, Chengdu 610031
    d Guangzhou Institute of Biomedicine and Health, Chinese Academy of Sciences, Guangzhou 510530

Received date: 2019-04-23

  Revised date: 2019-05-13

  Online published: 2019-06-03

Supported by

Project supported by the National Natural Science Foundation of China(21672030)

Abstract

Solanoeclepin A, first isolated from potato roots (Solanaceae Juss.) by Mulder et al., is an highly active hatching stimulant (0.3 g per hectare) of potato cyst nematode (PCN, Globodera rostochiensis and G. pallida) which causes severe damage to potato crops. Its complex chemical structure belongs to a rearranged tetranortriterpene and possesses extremely unique skeleton. Based on the known general biosynthesis of tetranortriterpenoids and Prof. Corey’s biomimetic synthesis of glycinoeclepin, a plausible biosynthetic pathway of solanoeclepin A is proposed. A schematic review on the synthetic studies towards solanoeclepin A is provided.

Cite this article

Mao Sun , Fayang Qiu , Wei-Dong Li . Recent Progresses in the Synthesis of Solanoeclepin A[J]. Chinese Journal of Organic Chemistry, 2019 , 39(10) : 2759 -2770 . DOI: 10.6023/cjoc201904055

References

[1] (a) Tan, Q. G.; Luo, X. D. Chem. Rev. 2001, 111, 7437.
[1] (b) Xiao, W. L.; Li, R. T.; Huang, S. X.; Pu, J. X.; Sun, H. D. Nat. Prod. Rep. 2008, 25, 871.
[1] (c) Li, R. T.; Zhao, Q. S.; Li, S. H.; Han, Q. B.; Sun, H. D.; Lu, Y.; Zhang, L. L.; Zheng, Q. T. Org. Lett. 2003, 5, 1023.
[2] (a) Xiao, Q.; Ren, W. W.; Chen, Z. X.; Sun, T. W.; Li, Y.; Ye, Q. D.; Gong, J. X.; Meng, F. K.; You, L.; Liu, Y. F.; Zhao, M. Z.; Xu, L. M.; Shan, Z. H.; Tang, Y. F.; Chen, J. H.; Yang, Z. Angew. Chem., Int. Ed. 2011, 50, 7373.
[2] (b) You, L.; Liang, X. T.; Xu, L. M.; Wang, Y. F.; Zhang, J. J.; Su, Q.; Li, Y. H.; Zhang, B.; Yang, S. L.; Chen, J. H.; Yang, Z. J. Am. Chem. Soc. 2015, 137, 10120.
[2] (c) Li, J.; Yang, P.; Yao, M.; Deng, J.; Li, A. J. Am. Chem. Soc. 2014, 136, 16477.
[2] (d) Kleinnijenhuis, R. A.; Timmer, B. J. J.; Lutteke, G.; Smits, J. M. M.; de Gelder, R.; van Maarseveen, J. H.; Hiemstra, H. Chem.-Eur. J. 2008, 14, 10683.
[2] (e) Wang, L.; Wang, H. T.; Li, Y. H.; Tang, P. P. Angew. Chem., Int. Ed. 2015, 54, 5732.
[2] (f) Goh, S. S.; Chaubet, G.; Gockel, B.; Cordonnier, M. A.; Baars, H.; Phillips, A. W.; Anderson, E. A. Angew. Chem., Int. Ed. 2015, 54, 12618.
[3] (a) Mulder, J. G.; Diepenhorst, P.; Brügge mann-Rotgans, I. E. M. WO 93020083, 1993 [Chem. Abstr. 1993, 118, 185844z].
[3] (b) Schenk, H.; Driessen, R. A. J.; de Gelder, R.; Goubitz, K.; Nieboer, H.; Brüggemann Rotgans, I. E. M.; Diepenhorst, P. Croat. Chem. Acta 1999, 72, 593.
[3] (c) Fukuzawa, A.; Furusaki, A.; Ikura, M.; Masamune, T. J. Chem. Soc., Chem. Commun. 1985, 222.
[3] (d) Murai, A.; Tanimoto, N.; Sakamoto, N.; Masamune, T. J. Am. Chem. Soc. 1988, 10, 1985.
[3] (e) Mori, K.; Watanabe, H. Pure Appl. Chem. 1989, 61, 543.
[3] (f) Corey, E. J.; Houpis, I. N. J. Am. Chem. Soc. 1990, 112, 8997.
[3] (g) Corey, E. J.; Hong, B. C. J. Am. Chem. Soc. 1994, 116, 3149.
[4] (a) Blaauw, R. H.; Brière, J.-F.; de Jong, R.; Benningshof, J. C. J.; van Ginkel, A. E.; Rutjes, F. P. J. T.; Fraanje, J.; Goubitz, K.; Schenk, H.; Hiemstra, H. Chem. Commun. 2000,1463.
[4] (b) Benningshof, J. C. J.; Blaauw, R. H.; van Ginkel, A. E. J. H; Rutjes, F. P. J. T.; Fraanje, J.; Goubitz, K.; Schenk, H.; Hiemstra, H. Chem. Commun. 2000, 1465.
[4] (c) Blaauw, R. H.; Brière, J. F.; de Jong, R.; Benningshof, J. C. J.; van Ginkel, A. E.; Fraanje, J.; Goubitz, K.; Schenk, H.; Rutjes, F. P. J. T.; Hiemstra, H. J. Org. Chem. 2001, 66. 233.
[4] (d) Brière, J.-F.; Blaauw, R. H.; Benningshof, J. C. J.; van Ginkel, A. E.; van Maarseveen, J. H.; Hiemstra, H. Eur. J. Org. Chem. 2001, 2371.
[4] (e) B laauw, R. H.; Benningshof, J. C. J.; van Ginkel, A. E.; van Maarseveen, J. H.; Hiemstra, H. Chem. Soc., Perkin Trans. 2001, 2250.
[4] (f) Benningshof, J. C. J.; Blaauw, R. H.; van Ginkel, A. E.; van Maarseveen, J. H.; Rutjes, F. P. J. T.; Hiemstra, H. J. Chem. Soc., Perkin Trans. 1 2002, 1693.
[4] (g) Benningshof, J. C. J.; IJsselstijn, M.; Wallner, S. R.; Koster, A. L.; Blaauw, R. H.; van Ginkel, A. E.; Brière, J.-F.; van Maarseveen, J. H.; Rutjes, F. P. J. T.; Hiemstra, H. J. Chem. Soc., Perkin Trans. 1, 2002, 1701.
[4] (h) Hue, B. T. B.; Dijkink, J.; Kuiper, S.; Larson, K. K.; Guziec, Jr. F. S.; Goubitz, K.; Fraanje, J.; Schenk, H.; van Maarseveen, J. H.; Hiemstra, H. Org. Biomol. Chem. 2003, 1. 4364.
[4] (i) Hue, B. T. B.; Dijkink, J.; Kuiper, S.; van Schaik, S.; van Maarseveen, J. H.; Hiemstra, H. Eur. J. Org. Chem. 2006, 127.
[4] (j) Lutteke, G.; Kleinnijenhuis, R. A.; Jacobs, I.; Wrigstedt, P. J.; Correia, A. C. A.; Nieuwenhuizen, R.; Hue, B. T. B.; Goubitz, K.; Peschar, R.; van Maarseveen, J. H.; Hiemstra, H. Eur. J. Org. Chem. 2011, 3146.
[4] (k) Kleinnijenhuis, R. A.; Timmer, B. J. J.; Lutteke, G.; Smits, J. M. M.; de Gelder, R.; van Maarseveen, J. H.; Hiemstra, H. Chem.-Eur. J. 2016, 22. 1266.
[5] (a) Tojo, S.; Isobe, M. Synthesis 2005,1237.
[5] (b) Adachi, M.; Yamauchi, E.; Komada, T.; Isobe, M. Synlett 2009, 1157.
[5] (c) Tsao, K. W.; Cheng, C. Y.; Isobe, M. Org. Lett. 2012, 14. 5274.
[5] (d) Chuang, H. Y.; Isobe, M. Org. Lett. 2014, 16. 4166.
[5] (e) Lin, Y. T.; Lin, F. Y.; Isobe, M. Org. Lett. 2014, 16. 5948.
[5] (f) Chuang, H. Y.; Isobe, M. TetrahedronOrg. Lett. 2017, 73. 2705.
[5] (g) Chuang, H. Y.; Isobe, M. J. Org. Chem. 2017, 82. 2045.
[6] (a) Komada, T.; Adachi, M.; Nishikawa, T. Chem. Lett. 2012, 41, 287.
[6] (b) Adachi, M.; Komada, T.; Nishikawa, T. J. Org. Chem. 2011, 76, 6942.
[6] (c) Adachi, M.; Torii, M.; Nishikawa, T. Synlett 2015, 26, 965.
[7] Liu, G.; Han, J. C.; Li, C. C. Tetrahedron 2017, 73, 3629.
[8] Sun, M.; Li, W. D Qiu, F. Y .; Org. Lett. 2019, 21, 644.
[9] Tanino, K.; Takahashi, M.; Tomata, Y.; Tokura, H.; Uehara, T.; Miyashita, M. Nat. Chem. 2011, 3, 484.
[10] (a) Chang, J. B.; Reiner, J.; Xie, J. X. Chem. Rev. 2005, 105, 4581.
[10] (b) Kuo, Y. H.; Kuo, L. Y.; Chen, C. F. J. Org. Chem. 1997, 62, 3242.
[11] (a) Chen, D. F.; Zhang, S. X.; Wang, H. K.; Zhang, S. Y.; Sun, Q. Z.; Cosentino, M.; Lee, K. H. J. Nat. Prod. 1999, 62, 94.
[11] (b) Sun, H. D.; Qiu, S. X.; Lin, L. Z.; Wang, Z. Y.; Lin, Z. W.; Pengsuparp, T.; Pezzuto, J. M.; Fong, H. H. S.; Cordell, C. A.; Farnsworth, N. R. J. Nat. Prod. 1996, 59, 525.
[12] (a) Mordue, A. J.; Blackwell, A. J. Insect Physiol. 1993, 39, 903.
[12] (b) Simmonds, M. S. J.; Blaney, W. M. Entomol. Exp. Appl. 1996, 80, 23.
[12] (c) Karnavar, G. K. Proc.-Indian Acad. Sci., Anim. Sci. 1987, 96, 341.
Outlines

/