Progress in Synthesis of 3,4-Fused Indole Alkaloids

doi:10.6023/cjoc201304035

Abstract

The indole nucleus is one of the most important heterocycles for its presence in a vast number of bioactive natural products, pharmaceuticals, and agrochemicals.Due to their widest spectrum of biological activity and some of them have been used in clinical trials, construction and functionalization of indoles have attracted considerable interests from synthetic and medicinal chemists for over a hundred years.Among the naturally occurring indole alkaloids, those containing 3,4-fused indole skeleton possess a major part and have been especially considered attractive synthetic targets because of their unique structure and biological activities.This review emphasized on the methodologies and strategies of construction of 3,4-fused indole skeleton, and their application in total synthesis of natural products.

Key words: indole alkaloids, 3,4-fused indoles, natural products, total synthesis

Cite this article

Shan Dong, Jia Yanxing. Progress in Synthesis of 3,4-Fused Indole Alkaloids[J]. Chin. J. Org. Chem., 2013, 33(06): 1144-1156.

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References

[1] For recent reviews on the synthesis of indoles, see: (a) Humphrey, G.R.; Kuethe, J.T.Chem.Rev.2006, 106, 2875.(b) Cacchi, S.; Fabrizi, G.Chem.Rev.2005, 105, 2873.(c) Gribble, G.W.J.Chem.Soc., Perkin Trans.1 2000, 1045.
[2] For total synthesis of dehydrobufotenine, see: (a) Peat, A.J.; Buchwald, S.L.J.Am.Chem.Soc. 1996, 118, 1028.(b) Jackson, B.; Hester, J.J.Org.Chem.1964, 29, 1158.
[3] For total synthesis of lysergic acid, see: (a) Liu, Q.; Jia, Y.Org.Lett. 2011, 13, 4810.(b) Iwata, A.; Inuki, S.; Oishi, S.; Fujii, N.; Ohno, H. J.Org.Chem.2011, 76, 5506.(c) Kurokawa, T.; Isomura, M.; Tokuyama, H.; Fukuyama, T.Synlett 2009, 775.
[4] For total synthesis of N-methylwelwitindolinone, see: (a) Huters, A.D.; Quasdorf, K.W.; Styduhar, E.D.; Garg, N.K.J.Am.Chem.Soc.2011, 133, 15797.(b) Bhat, V.; Allan, K.M.; Rawal, V.H.J.Am.Chem.Soc.2011, 133, 5798.
[5] For total synthesis of communesin F, see: (a) Yang, J.Wu, H.; Shen, L.; Qin, Y.J.Am.Chem.Soc. 2007, 129, 13794.(b) Zuo, Z.; Xie, W.; Ma, D.J.Am.Chem.Soc. 2010, 132, 13226.(c) Liu, P.; Seo, J.H.; Weinreb, S.M.Angew.Chem., Int.Ed.2010, 49, 2000.(d) Belmar, J.; Funk, R.L.J.Am.Chem.Soc.2012, 134, 16941.
[6] For total synthesis of dragmacidin E, see: Feldman, K.S.; Ngernmeesri, P.Org.Lett. 2011, 13, 5704.
[7] For total synthesis of decursivine, see: (a) Mascal, M.; Modes, K.V.; Durmus, A.Angew.Chem., Int.Ed. 2011, 50, 4445.(b) Qin, H.; Xu, Z.; Cui, Y.; Jia, Y.Angew.Chem., Int.Ed. 2011, 50, 4447.(c) Hu, W.; Qin, H.; Cui, Y.; Jia, Y.Chem.Eur.J. 2013, 19, 3139.(d) Sun, D.; Zhao, Q.; Li, C.Org.Lett.2011, 13, 5302.(e) Leduc, A.B.; Kerr, M.A.Eur.J.Org.Chem. 2007, 237;.(f) Koizumi, Y.; Kobayashi, H.; Wakimoto, T.; Furuta, T.; Fukuyama, T.; Kan, T.J.Am.Chem.Soc.2008, 130, 16854.
[8] For total synthesis of penitrem D, see: Smith, III.A.B.; Kanoh, N.; Ishiyama, H.; Noriaki, M.; Rainier, J.D.; Hartz, R.A.; Cho, Y.S.; Cui, H.; Moser, W.H.J.Am.Chem.Soc.2003, 125, 8228.
[9] For total synthesis of indolactam V, see: (a) Xu, Z.; Zhang, F.; Zhang, L.; Jia, Y.Org.Biomol.Chem.2011, 9, 2512.(b) Bronner, S.M.; Goetz, A.E.; Garg, N.K.Synlett 2011, 2599.(c) Bronner, S.M.; Goetz, A.E.; Garg, N.K.J.Am.Chem.Soc.2011, 133, 3832.(d) Meseguer, B.; Alonso-Díaz, D.; Griebenow, N.; Herget, T.; Waldmann, H.Angew.Chem., Int.Ed. 1999, 38, 2902.(e) Moreno, O.A.; Kishi, Y.J.Am.Chem.Soc.1996, 118, 8180.
[10] For total synthesis of diazonamide A, see: (a) Burgett, A.W.G.; Li, Q.; Wei, Q.; Harran, P.G.Angew.Chem., Int.Ed. 2003, 42, 4961.(b) Nicolaou, K.C.; Chen, D.Y.-K.; Huang, X.; Ling, T.; Bella, M.; Snyder, S.A.J.Am.Chem.Soc. 2004, 126, 12888.(c) Nicolaou, K.C.; Hao, J.; Reddy, M.V.; Rao, P.B.; Rassias, G.; Snyder, S.A.; Huang, X.; Chen, D.Y.-K.; Brenzovich, W.E.; Giuseppone, N.; Giannakakou, P.; O'Brate, A.J.Am.Chem.Soc. 2004, 126, 12897.(d) Knowles, R.R.; Carpenter, J.; Blakey, S.B.; Kayano, A.; Mangion, I.K.; Sinz, C.J.; MacMillan, D.W.C.Chem.Sci.2011, 2, 308.(e) Cheung, C.-M.; Goldberg, F.W.; Magnus, P.; Russell, C.J.; Turnbull, R.; Lynch, V.J.Am.Chem.Soc. 2007, 129, 12320.(f) Mai, C.-K.; Sammons, M.F.; Sammakia, T.Angew.Chem., Int.Ed. 2010, 49, 2397.
[11] (a) Kornfeld, E.C.; Fornefeld, E.J.; Kline, G.B.; Mann, M.J.; Morrison, D.E.; Jones, R.G.; Woodward, R.B.J.Am.Chem.Soc.1956, 78, 3087.(b) Kornfeld, E.C.; Fornefeld, E.J.; Kline, G.B.; Mann, M.J.; Jones, R.G.; Woodward, R.B.J.Am.Chem.Soc.1954, 76, 5256.
[12] (a) Szmuszkovicz, J.J.Org.Chem.1964, 29, 843.(b) Nagasaka, T.; Ohki, S.Chem.Pharm.Bull.1977, 25, 3023.
[13] (a) Nakatsuka, S.-i.; Miyazaki, H.; Goto, T.Tetrahedron Lett.1980, 21, 2817.(b) Lee, Y.S.; Min, B.J.; Park, Y.K.; Lee, J.Y.; Lee, S.J.; Park, H.Tetrahedron Lett.1999, 40, 5569.(c) Lee, Y.S.; Min, B.J.; Park, Y.K.; Lee, J.Y.; Lee, S.J.; Park, H.Tetrahedron 1999, 55, 12991.
[14] Teranishi, K.; Hayashi, S.; Nakatsuka, S.-I.; Goto, T.Tetrahedron Lett. 1994, 35, 8173.
[15] (a) Incze, M.; Dörnyei, G.; Moldvai, I.; Temesvári-Major, E.; Egyed, O.; Szántay, C.Tetrahedron 2008, 64, 2924.(b) Moldvai, I.; Temesvári-Major, E.; Incze, M.; Szentirmay, É.; Gács-Baitz, E.; Szántay, C.J.Org.Chem.2004, 69, 5993.
[16] Condie, G.C.; Channon, M.F.; Ivory, A.J.; Kumar, N.; Black, D.S.Tetrahedron 2005, 61, 4989.
[17] (a) Somei, M.; Seto, M.Heterocycles 2003, 60, 519.(b) Somei, M.; Teranishi, S.; Yamada, K.; Yamada, F.Chem.Pharm.Bull.2001, 49, 1159.(c) Yamada, K.; Namerikawa, Y.; Haruyama, T.; Miwa, Y.; Yanada, R.; Ishikura, M.Eur. J.Org.Chem. 2009, 33, 5752.
[18] Bergman, J.; Venemalm, L.; Gogoll, A.Tetrahedron 1990, 46, 6067.
[19] (a) Yonemitsu, O.; Cerutti, P.; Witcop, B.J.Am.Chem.Soc.1966, 88, 3941.(b) Naruto, S.; Yonemitsu, O.Tetrahedron Lett.1975, 16, 3399.(c) Naruto, S.; Yonemitsu, O.Chem.Pharm.Bull. 1980, 28, 900.
[20] (a) Kobayashi, T.; Spande, T.F.; Aoyagi, H.; Witcop, B. J.Med.Chem.1969, 12, 636.(b) Klohr, S.E.; Cassady, J.M.Synth.Commun.1988, 18, 671.
[21] (a) Mascal, M.; Moody, C.J.J.Chem.Soc., Chem.Commun.1988, 587.(b) Mascal, M.; Moody, C.J.J.Chem.Soc., Chem.Commun.1988, 589.(c) Beck, A.L.; Mascal, M.; Moody, C.J.; Slawin, A.M.Z.; Williams, D.J.; Coates, W.J.J.Chem.Soc., Perkin Trans.1 1992, 797.(d) Beck, A.L.; Mascal, M.; Moody, C.J.; Coates, W.J.J.Chem.Soc., Perkin Trans.1 1992, 813.(e) Mascal, M.; Moody, C.J.; Slawin, A.M.Z.; Williams, D.J.J.Chem.Soc., Perkin Trans.1 1992, 823.(f) Mascal, M.; Moody, C.J.; Morrell, A.I.; Slawin, A.M.Z.; Williams, D.J.J.Am.Chem.Soc.1993, 115, 813.(g) Mascal, M.; Wood, I.G.; Begley, M.J.; Batsanov, A.S.; Walsgrove, T.; Slawin, A.M.Z.; Williams, D.J.; Drake, A.F.; Siligardi, G.J.Chem.Soc., Perkin Trans.1 1996, 2427.
[22] (a) Feldman, K.S.; Ngernmeesri, P.Org.Lett. 2005, 7, 5449.(b) Feldman, K.S.; Ngernmeesri, P.Org.Lett.2011, 13, 5704.
[23] (a) Li, J.; Jeong, S.; Esser, L.; Harran, P.G.Angew.Chem., Int.Ed.2001, 40, 4765.(b) Burgett, A.W.G.; Li, Q.; Harran, P.G.Angew.Chem., Int.Ed. 2003, 42, 4961.
[24] Rafferty, R.J.; Williams, R.M.J.Org.Chem.2012, 77, 519.
[25] (a) Baran, P.S.; Thomas, J.; Maimone, T.J.; Richter, J.M.Nature 2007, 446, 404.(b) Xu, Q.; Dai, L.; You, S.Chem.Sci.2013, 4, 97.(c) Hellal, M.; Singh, S.; Cuny, G.D.J.Org.Chem.2012, 77, 4123.(d) Lim, H.J.; Gallucci, J.C.; RajanBabu, T.V.Org.Lett. 2010, 12, 2162.(e) Kalinin, A.V.; Chauder, B.A.; Rakhit, S.; Snieckus, V.Org.Lett.2003, 5, 3519.(f) Katayama, S.; Ae, N.; Nagata, R.J.Org.Chem. 2001, 66, 3474.(g) Horwell, D.C.; Nichols, P.D.; Ratcliffe, G.S.; Roberts, E.J.Org.Chem.1994, 59, 4418.(h) Peshkov, V.A.; Hove, S.V.; Donets, P.A.; Pereshivko, O.P.; Hecke, K.V.; Meervelt, L.V.; Van der Eycken, E.V.Eur.J.Org.Chem.2011, 1837.(i) Söderberg, B.C.G.; Hubbard, J.W.; Rector, S.R.; O'Neil, S.N.Tetrahedron 2005, 61, 3637.(j) Söderberg, B.C.G.; Rector, S.R.; O'Neil, S.N.Tetrahedron Lett.1999, 40, 3657.
[26] Baran, P.S.; Maimone, T.J.; Richter, J.M.Nature 2007, 446, 404.
[27] Martin, S.F.; Liras, S.J.Am.Chem.Soc.1993, 115, 10450.
[28] Liras, S.; Lynch, C.L.; Fryer, A.M.; Vu, B.T.; Martin, S.F.J.Am.Chem.Soc.2001, 123, 5918.
[29] Xu, Z.; Li, Q.; Zhang, L.; Jia, Y.J.Org.Chem. 2009, 74, 6859.
[30] (a) Greshock, T.J.; Funk, R.L.J.Am.Chem.Soc.2006, 128, 4946.(b) Huntley, R.J.; Funk, R.L.Org.Lett.2006, 8, 4775.
[31] (a) Petronijevic, F.; Timmons, C.; Cuzzupe, A.; Wipf, P.Chem.Commun.2009, 104.(b) Petronijevic, F.; Wipf, P.J.Am.Chem.Soc.2011, 133, 7704.
[32] Park, I.-K.; Park, J.; Cho, C.-G.Angew.Chem., Int.Ed.2012, 55, 2496.
[33] (a) Xu, Z.; Hu, W.; Zhang, F.; Li, Q.; Lu, Z.; Zhang, L.; Jia, Y.Synthesis 2008, 3981.(b) Hu, C.; Qin, H.; Cui, Y.; Jia, Y.Tetrahedron 2009, 65, 9075.(c) Xu, Z.; Li, Q.; Zhang, L.; Jia, Y.J.Org.Chem. 2009, 74, 6859.(d) Hu, W.; Zhang, F.; Xu, Z.; Liu, Q.; Cui, Y.; Jia, Y.Org.Lett. 2010, 12, 956.(e) Xu, Z.; Hu, W.; Liu, Q.; Zhang, L.; Jia, Y.J.Org.Chem. 2010, 75, 7626.(f) Liu, Y.; Zhang, L.; Jia, Y.Tetrahedron Lett.2012, 53, 684.(g) Jiang, D.; Xu, Z.; Jia, Y.Tetrahedron 2012, 68, 4225.
[34] Shan, D.; Gao, Y.; Jia, Y.Angew.Chem., Int.Ed.2013, 52, 4902.
[35] Breazzano, S.P.; Poudel, Y.B.; Boger, D.L.J.Am.Chem.Soc.2013, 135, 1600.

3,4-桥环吲哚类生物碱的合成研究进展