OALib Journal期刊
吡咯并菲啶酮构建方法学研究进展有机化学
DOI: 10.6023/cjoc201404041
Keywords: 吡咯并菲啶酮 ,方法学 ,偶联反应 ,金属催化 ,自由基反应
Abstract:
吡咯并菲啶酮母核广泛存在于石蒜科生物碱中，该系列的生物碱展示出很多有价值的生物活性.吡咯并菲啶酮独特的结构吸引了众多学者对其合成进行探索研究.在过去的几十年中，很多有价值的构建方法被报道，其中主要以过渡金属催化或自由基历程等分子内或分子间偶联反应为主.对其构建方法学进行了系统地综述.
References
[1] (a) Pigni, N. B.; Ríos-Ruiz, S.; Martínez-Francés, V.; Nair, J. J.; Viladomat, F.; Codina, C.; Bastida, J. J. Nat. Prod. 2012, 75, 1643. [2] (c) Ramadan, M. A.; Kamel, M. S.; Ohtani, K.; Kasai, R.; Yamasaki, K. Phytochemistry 2000, 54, 891. [3] (e) Ghosal, S.; Saini, K. S.; Frahm, A. W. Phytochemistry 1983, 22, 2305. [4] (a) Min, B. S.; Gao, J. J.; Nakamura, N.; Kim, Y. H.; Hattori, M. Chem. Pharm. Bull. 2001, 49, 1217. [5] Chattopadhyay, S.; Chattopadhyay, U.; Mathur, P. P.; Saini, K. S.; Ghosal, S. Planta Med. 1983, 49, 252. [6] (a) Johansson Seechurn, C. C. C.; Kitching, M. O.; Colacot, T. J.; Snieckus, V. Angew. Chem. Int. Ed. 2012, 51, 5062. [7] (c) Neufeldt, S. R.; Sanford, M. S. Acc. Chem. Res. 2012, 45, 936. [8] (e) Sun, C.-L.; Li, B.-J.; Shi, Z.-J. Chem. Rev. 2011, 111, 1293. [9] (g) Roger, J.; Gottumukkala, A. L.; Doucet, H. ChemCatChem 2010, 2, 20. [10] (i) Chen, X.; Engle, K. M.; Wang, D.-H.; Yu, J.-Q. Angew. Chem., Int. Ed. 2009, 48, 5094. [11] (a) You, S.-L.; Xia, J.-B. Top. Curr. Chem. 2010, 292, 165. [12] (b) Zhao, L.; Li, Z.; Chang, L.; Xu, J.; Yao, H.; Wu, X. Org. Lett. 2012, 14, 2066. [13] (d) Wu, K.-J.; Dai, L.-X.; You, S.-L. Org. Lett. 2012, 14, 3772. [14] (e) Lv, J.; Liu, Q.; Tang, J.; Perdih, F.; Kranjc, K. Tetrahedron Lett. 2012, 53, 5248. [15] (g) Wang, C.; Piel, I.; Glorius, F. J. Am. Chem. Soc. 2009, 131, 4194. [16] (i) Zhang, H.; Ferreira, E. M.; Stoltz, B. M. Angew. Chem., Int. Ed. 2004, 43, 6144. [17] (k) Ferreira, E. M.; Stoltz, B. M. J. Am. Chem. Soc. 2003, 125, 9578. [18] Grigg, R.; Teasdale, A.; Sridharan, V. Tetrahedron Lett. 1991, 32, 3859. [19] Kn？lker, H.-J.; Filali, S. Synlett 2003, 1752. [20] (a) Pinto, A. C.; Silva, F. S. Q.; Silva, R. B. Tetrahedron Lett. 1994, 35, 8923. [21] Torres, J. C.; Pinto, A. C.; Garden, S. J. Tetrahedron 2004, 60, 9889. [22] Umemoto, H.; Dohshita, M.; Hamamoto, H.; Miki, Y. Heterocycles 2011, 83, 1111. [23] Cong, W.; Zhao, L.; Wu, X.; Xu, J.; Yao, H. Tetrahedron 2014, 70, 312. [24] (a) Xie, Y.; Yang, Y.; Huang, L.; Zhang, X.; Zhang, Y. Org. Lett. 2012, 14, 1238. [25] Rosen, B. M.; Percec, V. Chem. Rev. 2009, 109, 5069. [26] Tsuge, O.; Hatta, T.; Tsuchiyama, H. Chem. Lett. 1998, 155. [27] Ziegler, F. E.; Chliwner, I.; Fowler, K. W.; Kanfer, S. J.; Kuo, S. J.; Sinha, N. D. J. Am. Chem. Soc. 1980, 102, 790. [28] Hiroya, K.; Itoh, S.; Sakamoto, T. J. Org. Chem. 2004, 69, 1126. [29] Harutyunyan, S. R.; den Hartog, T.; Geurts, K.; Minnaard, A. J.; Feringa, B. L. Chem. Rev. 2008, 108, 2824. [30] For selected examples, see: [31] (a) Fodor, G.; Nagubandi, S. Tetrahedron 1980, 36, 1279. [32] (c) Su, B.; Chen, F.; Wang, Q. J. Org. Chem. 2013, 78, 2775. [33] Banwell, M. G.; Bissett, B. D.; Busato, S.; Cowden, C. J.; Hockless, D. C. R.; Holman, J. W.; Read, R. W.; Wu, A. W. J. Chem. Soc., Chem. Commun. 1995, 2551. [34] Siddiqui, M. A.; Snieckus, V. Tetrahedron Lett. 1990, 31, 1523. [35] Mentzel, U. V.; Tanner, D.; T？nder, J. E. J. Org. Chem. 2006, 71, 5807. [36] Kim, H. S.; Banwell, M. G.; Willis, A. C. J. Org. Chem. 2013, 78, 5103. [37] For selected examples, see: [38] (b) Liu, Y.; Nappi, M.; Arceo, E.; Vera, S.; Melchiorre, P. J. Am. Chem. Soc. 2011, 133, 15212. [39] (d) Jiang, X.; Wang, R. Chem. Rev. 2013, 113, 5515. [40] Boger, D. L.; Wolkenberg, S. E. J. Org. Chem. 2000, 65, 9120. [41] Martin, S. F. In The Alkaloids, Ed.: Brossi, A., Academic Press, New York, 1987, Vol. 30, Chapter 3, p. 251. [42] (b) Wang, L.; Zhang, X.-Q.; Yin, Z.-Q.; Wang, Y.; Ye, W.-C. Chem. Pharm. Bull. 2009, 57, 610. [43] (d) Ghosal, S.; Lochan, R.; Kumar, A. Y.; Srivastava, R. S. Phytochemistry 1985, 24, 1825. [44] (f) Ghosal, S.; Rao, P. H.; Jaiswal, D. K.; Kumar, Y.; Frahm, A. W. Phytochemisrty 1981, 20, 2003. [45] (b) Ali, A. A.; Mesbah, M. K.; Frahm, A. W. Planta Med. 1981, 43, 407. [46] (c) Zee-Cheng, R. K.-Y.; Yan, S.-J.; Cheng, C. C. J. Med. Chem. 1978, 21, 199. [47] For selected reviews on transition-metal catalyzed functionalization of arenes, see: [48] (b) Kuhl, N.; Hopkinson, M. N.; Wencel-Delord, J.; Glorius, F. Angew. Chem., Int. Ed. 2012, 51, 10236. [49] (d) Bras, J. L.; Muzart, J. Chem. Rev. 2011, 111, 1170. [50] (f) Liu, C.; Zhang, H.; Shi, W.; Lei, A. Chem. Rev. 2011, 111, 1780. [51] (h) Johansson, C. C. C.; Colacot, T. J. Angew. Chem., Int. Ed. 2010, 49, 676. [52] For a selected review on palladium-catalyzed intramolecular cylization of heteroarenes, see: [53] For selected examples, see: [54] (c) Piou, T.; Neuville, L.; Zhu, J. Tetrahedron 2013, 69, 4415. [55] (f) Yamuna, E.; Zeller, M.; Prasad, K. J. R. Tetrahedron Lett. 2011, 52, 6030. [56] (h) Rudolph, A.; Rackelmann, N.; Turcotte-Savard, M.-O.; Lautens, M. J. Org. Chem. 2009, 74, 289. [57] (j) Huang, Q.; Fazio, A.; Dai, G.; Campo, M. A.; Larock, R. C. J. Am. Chem. Soc. 2004, 126, 7460. [58] (l) Campo, M. A.; Huang, Q.; Yao, T.; Tian, Q.; Larock, R. C. J. Am. Chem. Soc. 2003, 125, 11506. [59] Sakamoto, T.; Yasuhara, A.; Kondo, Y.; Yamanaka, H. Heterocycles 1993, 36, 2597. [60] For selected examples, see: [61] (b) Garden, S. J.; Silva, R. B.; Pinto, A. C. Tetrahedron 2002, 58, 8399. [62] Miki, Y.; Shirokoshi, H.; Matsushita, K. Tetrahedron Lett. 1999, 40, 4347. [63] Miki, Y.; Umemoto, H.; Dohshita, M.; Hamamoto, H. Tetrahedron Lett. 2012, 53, 1924. [64] For selected examples, see: [65] (b) Wang, Z.-Q.; Zhang, W.-W.; Gong, L.-B.; Tang, R.-Y.; Yang, X.-H.; Liu, Y.; Li, J.-H. Angew. Chem., Int. Ed. 2011, 50, 8968. [66] Lauk, U.; Dürst, D.; Fischer, W. Tetrahedron Lett. 1991, 32, 65. [67] Sperotto, E.; van Klink, G. P.; van Koten, G.; de Vries, J. G. Dalton Trans. 2010, 39, 10338. [68] Harrowven, D. C.; Lai, D.; Lucas, M. C. Synthesis 1999, 1300. [69] Ganton, M. D.; Kerr, M. A. Org. Lett. 2005, 7, 4777. [70] Iwao, M.; Takehara, H.; Obta, S.; Watanabe, M. Heterocycles 1994, 38, 1717. [71] Hutchings, R. H.; Meyers, A. I. J. Org. Chem. 1996, 61, 1004. [72] (b) Medley, J. W.; Movassaghi, M. Org. Lett. 2013, 15, 3614. [73] (d) Adachi, S.; Onozuka, M.; Yoshida, Y.; Ide, M.; Saikawa, Y.; Nakata, M. Org. Lett. 2014, 16, 358. [74] Hiroya, K.; Itoh, S.; Sakamoto, T. J. Org. Chem. 2004, 69, 1126. [75] Hartung, C. G.; Fecher, A.; Chapell, B.; Snieckus, V. Org. Lett. 2003, 5, 1899. [76] Robbins, D. W.; Boebel, T. A.; Hartwig, J. F. J. Am. Chem. Soc. 2010, 132, 4068. [77] Pereira, M. M. A.; Prabhakar, S.; Lobo, A. M. J. Nat. Prod. 1996, 59, 744. [78] (a) Jia, Z.-J.; Jiang, H.; Li, J.-L.; Gschwend, B.; Li, Q.-Z.; Yin, X.; Grouleff, J.; Chen, Y.-C.; J？rgensen, K. A. J. Am. Chem. Soc. 2011, 133, 5053. [79] (c) Lin, S.; Ischay, M. A.; Fry, C. G.; Yoon, T. P. J. Am. Chem. Soc. 2011, 133, 19350. For selected reviews, see: [80] (e) Funel, J. A.; Abele, S. Angew. Chem., Int. Ed. 2013, 52, 3822.
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