Synthetic Progress of Fusarisetin A

doi:10.6023/cjoc201210027

Chin. J. Org. Chem. ›› 2013, Vol. 33 ›› Issue (02): 259-266.DOI: 10.6023/cjoc201210027 Previous Articles Next Articles

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Fusarisetin A的合成研究进展

尹军, 孔丽丽, 高栓虎

华东师范大学化学系上海市绿色化学与化工过程绿色化重点实验室上海 200062

收稿日期:2012-10-16 修回日期:2012-11-06 发布日期:2012-11-07
通讯作者: 高栓虎 E-mail:shgao@chem.ecnu.edu.cn
基金资助:
国家自然科学基金(Nos. 21102045, 21272076);“浦江人才计划”(No. 11PJ1402800)和“新博士点教师基金”(No. 20110076120022)资助项目.

Synthetic Progress of Fusarisetin A

Yin Jun, Kong Lili, Gao Shuanhu

Shanghai Key Laboratory of Green Chemistry and Chemical Processes, Department of Chemistry, East China Normal University, Shanghai 200062

Received:2012-10-16 Revised:2012-11-06 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).

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

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Yin Jun, Kong Lili, Gao Shuanhu. Synthetic Progress of Fusarisetin A[J]. Chin. J. Org. Chem., 2013, 33(02): 259-266.

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[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.

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Fusarisetin A的合成研究进展

Synthetic Progress of Fusarisetin A

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