Chinese Journal of Organic Chemistry >
Progress in the Synthesis of Spirotryprostatin Alkaloids
Received date: 2016-03-18
Revised date: 2016-05-17
Online published: 2016-06-01
Supported by
Project supported by the Scientific Research Project Item for Key Laboratory of Shaanxi Province Education Department (No.2010JS056).
Spirotryprostatin is one of the alkaloids which contains the spiro-indolyl diketopiperazine structure. It is structurally characterized by indole moiety connected to diketopiperazine moiety via the spiro quaternary carbon chiral center. The combination of the structure of spiro-indoyl and diketopiperazine has demonstrated the special physiological and pharmacological activities, especially the excellent inhibitory activity to cell cycle. In recent years, The synthesis of spirotryprostatin has attracted much attention, according to the formation of the spirocyclic chiral center. The total synthetic efforts towards spirotryprostatin alkaloids are presented.
Ma Yangmin , Fan Chao . Progress in the Synthesis of Spirotryprostatin Alkaloids[J]. Chinese Journal of Organic Chemistry, 2016 , 36(10) : 2380 -2396 . DOI: 10.6023/cjoc201603031
[1] Ma, Y.; Liu, B. Chin. J. Org. Chem. 2010, 30, 1624(in Chi-nese). (马养民, 刘斌有机化学, 2010, 30, 1624.)
[2] Jossang, A.; Jossang, P.; Hadi, H. A.; Sevenet, T.; Bodo, B. J. Org. Chem. 1991, 56, 6527.
[3] Pellegrini, C.; Weber, M.; Borschberg, H.-J. Helv. Chim. Acta 1996, 79, 151.
[4] Elderfield, R. C.; Gilman, R. E. Phytochemistry 1972, 11, 339.
[5] Dideberg, O.; Lamotte-Brasseur, J.; Dupont, L.; Campsteyn, H.; Vermeire, M.; Angenot, L. Acta Crystallogr., Sect. B:Struct. Crystallogr. Cryst. Chem. 1977, 33, 1796.
[6] Kornet, M. J.; Thio, A. P. J. Med. Chem. 1976, 19, 892.
[7] Bignan, G. C.; Battista, K.; Connolly, P. J.; Orsini, M. J.; Liu, J.; Middleton, S. A.; Reitz, A. B. Biorg. Med. Chem. Lett. 2005, 15, 5022.
[8] Malinakova, H. C.; Liebeskind, L. S. Org. Lett. 2000, 2, 4083.
[9] Antonchick, A. P.; Gerding-Reimers, C.; Catarinella, M.; Schurmann, M.; Preut, H.; Ziegler, S.; Rauh, D.; Waldmann, H. Nat. Chem. 2010, 2, 735.
[10] Brandman, H. A. J. Heterocycl. Chem. 1973, 10, 383.
[11] Yu, B.; Yu, D. Q.; Liu, H. M. Eur. J. Med. Chem. 2015, 97, 673.
[12] Rajanarendar, E.; Ramakrishna, S.; Govardhan Reddy, K.; Nagaraju, D.; Reddy, Y. N. Bioorg. Med. Chem. Lett. 2013, 23, 3954.
[13] Santos, M. M. M. Tetrahedron 2014, 70, 9735.
[14] Huang, R.; Zhou, X.; Xu, T.; Yang, X.; Liu, Y. Chem. Biodiversity 2010, 7, 2809.
[15] Zhao, Y.; Liu, L.; Sun, W.; Lu, J.; McEachern, D.; Li, X.; Yu, S.; Bernard, D.; Ochsenbein, P.; Ferey, V.; Carry, J. C.; Deschamps, J. R.; Sun, D.; Wang, S. J. Am. Chem. Soc. 2013, 135, 7223.
[16] Mali, P. R.; Chandrasekhara Rao, L.; Bangade, V. M.; Shirsat, P. K.; George, S. A.; Jagadeesh babu, N.; Meshram, H. M. New J. Chem. 2016, 40, 2225.
[17] Cui, C.-B.; Kakeya, H.; Osada, H. Tetrahedron 1996, 52, 12651.
[18] Cui, C.-B.; Kakeya, H.; Osada, H. J. Antibiotics 1996, 49, 832.
[19] Wang, F.; Fang, Y.; Zhu, T.; Zhang, M.; Lin, A.; Gu, Q.; Zhu, W. Tetrahedron 2008, 64, 7986.
[20] Afiyatullov, S.; Zhuravleva, O.; Chaikina, E.; Anisimov, M. Chem. Nat. Compd. 2012, 48, 95.
[21] Anisimov, M.; Chaikina, E.; Afiyatullov, S.; Klykov, A. Int. J. Res. Rev. Appl. Sci. 2012, 13, 326.
[22] Edmondson, S; Danishefsky, S. J. Angew. Chem. 1998, 37, 1138.
[23] Trost, B.; Brennan, M. Synthesis 2009, 3003.
[24] Bertamino, A.; Aquino, C.; Sala, M.; Simone, N.; Mattia, C. A.; Erra, L.; Musella, S.; Iannelli, P.; Carotenuto, A.; Grieco, P.; Novellino, E.; Campiglia, P.; Gomez-Monterrey, I. Bioorg. Med. Chem. 2010, 18, 4328.
[25] Edmondson, S.; Danishefsky, S. J.; Sepp-Lorenzino, L.; Rosen, N. J. Am. Chem. Soc. 1999, 121, 2147.
[26] Wang, H.; Ganesan, A. J. Org. Chem. 2000, 65, 4685.
[27] Wang, H.; Ganesan, A. Tetrahedron Lett. 1997, 38, 4327.
[28] Wang, H.; Ganesan, A. Org. Lett. 1999, 1, 1647.
[29] Wu, H, M.S. Thesis, Shaanxi University of Science & Technology, Xi'an, 2013(in Chinese). (吴昊, 硕士论文, 陕西科技大学, 西安, 2013.)
[30] Ma, Y.; Wu, H.; Zhang, J.; Li, Y. Chirality 2013, 25, 656.
[31] Trost, B. M.; Cramer, N.; Silverman, S. M. J. Am. Chem. Soc. 2007, 129, 12396.
[32] Chen, X. H.; Zhang, W. Q.; Gong, L. Z. J. Am. Chem. Soc. 2008, 130, 5652.
[33] Chen, X. H.; Wei, Q.; Luo, S. W.; Xiao, H.; Gong, L. Z. J. Am. Chem. Soc. 2009, 131, 13819.
[34] Liu, T. L.; Xue, Z. Y.; Tao, H. Y.; Wang, C. J. Org. Biomol. Chem. 2011, 9, 1980.
[35] Fejes, I.; Nyerges, M.; Szöllõsy, Á.; Blaskó, G.; Tõke, L. Tetrahedron 2001, 57, 1129.
[36] Ding, K.; Wang, G.; Deschamps, J. R.; Parrish, D. A.; Wang, S. Tetrahedron Lett. 2005, 46, 5949.
[37] Zubia, A.; Mendoza, L.; Vivanco, S.; Aldaba, E.; Carrascal, T.; Lecea, B.; Arrieta, A.; Zimmerman, T.; Vidal-Vanaclocha, F.; Cossio, F. P. Angew. Chem., Int. Ed. 2005, 44, 2903.
[38] Yang, Q. L.; Xie, M. S.; Xia, C.; Sun, H. L.; Zhang, D. J.; Huang, K. X.; Guo, Z.; Qu, G. R.; Guo, H. M. Chem. Commun. 2014, 50, 14809.
[39] Sebahar, P. R.; Williams, R. M. J. Am. Chem. Soc. 2000, 122, 5666.
[40] Sebahar, P. R.; Osada, H.; Usui, T.; Williams, R. M. Tetrahedron 2002, 58, 6311.
[41] Onishi, T.; Sebahar, P. R.; Williams, R. M. Org. Lett. 2003, 5, 3135.
[42] Onishi, T.; Sebahar, P. R.; Williams, R. M. Tetrahedron 2004, 60, 9503.
[43] Antonchick, A. P.; Schuster, H.; Bruss, H.; Schürmann, M.; Preut, H.; Rauh, D.; Waldmann, H. Tetrahedron 2011, 67, 10195.
[44] Narayan, R.; Potowski, M.; Jia, Z. J.; Antonchick, A. P.; Wald-mann, H. Acc. Chem. Res. 2014, 47, 1296.
[45] Cheng, M. N.; Wang, H.; Gong, L. Z. Org. Lett. 2011, 13, 2418.
[46] Overman, L. E.; Rosen, M. D. Angew. Chem., Int. Ed. 2000, 39, 4596.
[47] Trost, B. M.; Stiles, D. T. Org. Lett. 2007, 9, 2763.
[48] Kitahara, K.; Shimokawa, J.; Fukuyama, T. Chem. Sci. 2014, 5, 904.
[49] von Nussbaum, F.; Danishefsky, S. J. Angew. Chem., Int. Ed. 2000, 39, 2175.
[50] Bagul, T. D.; Lakshmaiah, G.; Kawabata, T.; Fuji, K. Org. Lett. 2002, 4, 249.
[51] Meyers, C.; Carreira, E. M. Angew. Chem., Int. Ed. 2003, 115, 718.
[52] Marti, C.; Carreira, E. M. J. Am. Chem. Soc. 2005, 127, 11505.
[53] Miyake, F. Y.; Yakushijin, K.; Horne, D. A. Angew. Chem., Int. Ed. 2004, 43, 5357.
[54] Miyake, F. Y.; Yakushijin, K.; Horne, D. A. Org. Lett. 2004, 6, 4249.
[55] Coote, S. C.; Quenum, S.; Procter, D. J. Org. Biomol. Chem. 2011, 9, 5104.
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