SIOC 中文
CJOG
Adv search

Chinese Journal of Organic Chemistry >

2013 , Vol. 33 >Issue 02: 259 - 266

DOI: https://doi.org/10.6023/cjoc201210027

Reviews

Synthetic Progress of Fusarisetin A

  • Yin Jun ,
  • Kong Lili ,
  • Gao Shuanhu
Expand
  • Shanghai Key Laboratory of Green Chemistry and Chemical Processes, Department of Chemistry, East China Normal University, Shanghai 200062

Received date: 2012-10-16

  Revised date: 2012-11-06

  Online published: 2012-11-07

Supported by

Project supported by the National Natural Science Foundation of China (Nos. 21102045, 21272076), the Shanghai “Pujiang Program” (No. 11PJ1402800) and the Research Fund for the Doctoral Programof Higher Education of China (No. 20110076120022).

Fold

Abstract

Fusarisetin A, a new tetramic acid type natural product, contains a 6-6-5-5-5 fused pentacycles and ten stereocenters. Fusarisetin A displays significant inhibition of acinar morphogenesis as well as cell migration and invasion, and shows the potency for selective inhibition of cancer cell metastasis. This review summarizes the synthetic progress of fusarisetin A since its discovery.

Key words： fusarisetin A; tetramic acid; tumor-cell migration; antitumor; total synthesis

Cite this article

Yin Jun , Kong Lili , Gao Shuanhu . Synthetic Progress of Fusarisetin A[J]. Chinese Journal of Organic Chemistry, 2013 , 33(02) : 259 -266 . DOI: 10.6023/cjoc201210027

References

[1] For isolation and characterization of equisetin, see: (a) Burmeister, H. R.; Bennett, G. A.; Vesonder, R. F.; Hesseltine, C. W. Antimicrob. Agents Chemother. 1974, 5, 634.
(b) Phillips, N. J.; Goodwin, J. T.; Fraiman, A.; Cole, R. J.; Lynn, D. G. J. Am. Chem. Soc. 1989, 111, 8223. For biosynthesis, see:
(c) Sims, J. W.; Fillmore, J. P.; Warner, D. D.; Schmidt, E. W. Chem. Commun. 2005, 186. For total syntheses, see:
(d) Turos, E.; Audia, J. E.; Danishefsky, S. J. J. Am. Chem. Soc. 1989, 111, 8231.
(e) Burke, L. T.; Dixon, D. J.; Ley, S. V.; Rodr_guez, F. Org. Lett. 2000, 2, 3611.
(f) Kumiko, Y. K.; Shindo, M.; Shishido, K. Tetrahedron Lett. 2001, 42, 2517.
(g) Burke, L. T.; Dixon, D. J.; Ley, S. V.; Rodr_guez, F. Org. Biomol. Chem. 2005, 3, 274.

[2] Singh, S. B.; Goetz, M. A.; Jones, E. T.; Bills, G. F.; Giacobbe, R. A.; Herram, L.; Stevens-Miles, S.; Williams, D. L. J. Org. Chem. 1995, 60, 7040.

[3] Pornpakakul, S.; Roengsumran, S.; Deechangvipart, S.; Petsom, A.; Muangsin, N.; Ngamrojnavanich, N.; Sriubolmas, N.; Chaichit, N.; Ohta, T. Tetrahedron Lett. 2007, 48, 651.

[4] (a) Singh, S. B.; Zink, D. L.; Heimbach, B.; Genilloud, O.; Teran, A.; Silverman, K. C.; Lingham, R. B.; Felock, P.; Hazuda, D. C. Org. Lett. 2002, 4, 1123.
(b) Wang, L. J.; Floreancig, P. E. Org. Lett. 2004, 6, 569.
(c) Dineen, T. A.; Roush, W. R. Org. Lett. 2005, 7, 1355.
(d) Sun, H. K.; Abbott, J. R.; Roush, W. R. Org. Lett. 2011, 13, 2734.

[5] Royles, B. J. L. Chem. Rev. 1995, 95, 1981.

[6] Schobert, R.; Schlenk, A. Bioorg. Med. Chem. 2008, 16, 4203.

[7] Liang, Y.; Ke, S. Y.; Wang. K. M.; Yang, Z. W. Chin. J. Org. Chem. 2010, 30, 1801 (in Chinese). (梁英, 柯少勇, 王开梅, 杨自文, 有机化学, 2010, 30, 1801.)

[8] Jang, J. H.; Asami, Y.; Jang, J. P.; Kim, S. O.; Moon, D. O.; Shin, K. S.; Hashizume, D.; Muroi, M.; Saito, T.; Oh, H.; Kim, B. Y.; Osada, H.; Ahn, J. S. J. Am. Chem. Soc. 2011, 133, 6865.

[9] Deng, J.; Zhu, B.; Lu, Z. Y.; Yu, H. X.; Li, A. J. Am. Chem. Soc. 2012, 134, 920.

[10] Xu, J.; Caro-Diaz, E. J. E.; Trzoss, L.; Theodorakis, E. A. J. Am. Chem. Soc. 2012, 134, 5072.

[11] Yin, J.; Wang, C.; Kong, L. L.; Cai, S. J.; Gao, S. H. Angew. Chem., Int. Ed. 2012, 51, 7786.

[12] Xu, J.; Caro-Diaz, E. J. E.; Lacoske, M. H.; Hung, C. I.; Jamora, C.; Theodorakis, E. A. Chem. Sci. 2012, 3, 3378.
Options
Outlines

/

〈 〉