Research Progress in Synthesis of Renieramycin-Type Alkaloids

doi:10.6023/cjoc201504003

Abstract

Marine tetrahydroisoquinoline alkaloids have attracted much attention in the fields of chemistry, biology and medicine over the past forty years because of their remarkable antitumor and antimicrobial activities. Among them, renieramycins is a big group, which consists of renieramycins A~Y, jorunnamycins A~C and jorumycin. A number of renieramycins and their analogues showed nanomolar inhibitory effects in a panel of human tumor cell lines. Therefore, along with other tetrahydroisoquinoline antitumor antibiotics, renieramycins are one of hotspots in the synthetic study of natural products. Progresses on the synthesis of renieramycin-type alkaloids are reviewed in terms of the key strategies employed.

Key words: tetrahydroisoquinoline, renieramycin-type alkaloids, natural product, total synthesis

Cite this article

Song Yuting, Hu Lingling, Chen Ruijiao, Chen Xiaochuan. Research Progress in Synthesis of Renieramycin-Type Alkaloids[J]. Chin. J. Org. Chem., 2015, 35(8): 1627-1640.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[1] (a) Scott, J. D.; Williams, R. M. Chem. Rev. 2002, 102, 1669. (b) Siengalewicz, P.; Rinner, U.; Mulzer, J. Chem. Soc. Rev. 2008, 37, 2676.
[2] (a) Rinehart, K. L. Med. Res. Rev. 2000, 20, 1. (b) Avendano, C.; de la Cuesta, E. Curr. Org. Synth. 2009, 6, 143. (c) Tang M.; Tang G. Chin. J. Org. Chem. 2012, 32, 1568 (in Chinese). (韩莹, 孙晶, 孙岩, 高红, 颜朝国, 有机化学, 2012, 32, 1568.)
[3] Frincke, J. M.; Faulkner, D. J. J. Am. Chem. Soc. 1982, 104, 265.
[4] (a) Wright, A. E.; Forleo, D. A.; Gunawardana, G. P.; Gunasekera, S. P.; Koehn, F. E.; McConnell, O. J. J. Org. Chem. 1990, 55, 4508. (b) Rinehart, K. L.; Holt, T. G.; Fregeau, N. L.; Stroh, J. G.; Keifer, P. A.; Sun, F.; Li, L. H.; Martin, D. G. J. Org. Chem. 1990, 55, 4512. (c) Sakai, R.; Rinehart, K. L.; Guan, Y.; Wang, A. H.-J. Proc. Natl. Acad. Sci. U. S. A. 1992, 89, 11456. (d) Sakai, R.; Jares-Erijman, E. A.; Manzanares, I.; Elipe, M. V. S.; Rinehart, K. L. J. Am. Chem. Soc. 1996, 118, 9017. (e) Tian, M.; Li, S.; Row, K. Chin. J. Chem. 2012, 30, 43.
[5] (a) Schoffski, P.; Wolter, P.; Clement, P.; Sciot, R.; Wever, I. D.; Wozniak, A.; Stefan, C.; Dumez, H. Future Oncol. 2007, 3, 381. (b) Carter, N. J.; Keam, S. J. Drugs 2007, 67, 2257. (c) Cuevas, C.; Francesch, A. Nat. Prod. Rep. 2009, 26, 322. (d) Molinski, T. F.; Dalisay, D. S.; Lievens, S. L.; Saludes, J. P. Nat. Rev. Drug Discovery 2009, 8, 69.
[6] Brodowicz, T. Future Oncol. 2014, 10(8 Suppl.), 1.
[7] (a) Ding, Z. W.; Tang, H.; Zhang, W. Pharm. Care Res. 2011, 11, 325 (in Chinese). (丁肇卫, 汤华, 张文, 药学服务与研究, 2011, 11, 325.) (b) Blay, J.-Y. Future Oncol. 2014, 10(8 Suppl.), 7. (c) Zanardi, E.; Maruzzo, M.; Montesco, M. C.; Roma, A.; Rastrelli, M.; Basso, U. Anticancer Drug 2014, 25, 1227. (d) Mascilini, F.; Amadio, G.; Di Stefano, M. G.; Ludovisi, M.; Di Legge, A.; Conte, C.; De Vincenzo, R.; Ricci, C.; Masciullo, V.; Salutari, V.; Scambia, G.; Ferrandina, G. OncoTargets Ther. 2014, 7, 1273.
[8] For the total synthesis of ecteinascidin 743, see: (a) Corey, E. J.; Gin, D. Y.; Kania, R. S. J. Am. Chem. Soc. 1996, 118, 9202. (b) Endo, A.; Yanagisawa, A.; Abe, M.; Tohma, S.; Kan, T.; Fukuyama, T. J. Am. Chem. Soc. 2002, 124, 6552. (c) Chen, J.; Chen, X.; Bois-Choussy, M.; Zhu, J. J. Am. Chem. Soc. 2006, 128, 87. (d) Kawagishi, F.; Toma, T.; Inui, T.; Yokoshima, S.; Fukuyama, T. J. Am. Chem. Soc. 2013, 135, 13684.
[9] For the formal total synthesis of ecteinascidin 743, see: (a) Zheng, S.; Chan, C.; Furuuchi, T.; Wright, B. J. D.; Zhou, B.; Guo, J.; Danishefsky, S. J. Angew. Chem., Int. Ed. 2006, 45, 1754. (b) Fishlock, D.; Williams, R. M. J. Org. Chem. 2008, 73, 9594.
[10] For the total synthesis of ecteinascidin 770, see: Chen, J.; Chen, X.; Willot, M.; Zhu, J. Angew. Chem., Int. Ed. 2006, 45, 8028.
[11] For the semisynthesis of ecteinascidin 743 and other ecteinascidins, see: (a) Cuevas, C.; Pérez, M.; Martin, M. J.; Chicharro, J. L.; Fernández-Rivas, C.; Flores, M.; Francesch, A.; Gallego, P.; Zarzuelo, M.; de la Calle, F.; García, J.; Polanco, C.; Rodríguez, I.; Manzanares, I. Org. Lett. 2000, 2, 2545. (b) Menchaca, R.; Martínez, V.; Rodríguez, A.; Rodríguez, N.; Flores, M.; Gallego, P.; Manzanares, I.; Cuevas, C. J. Org. Chem. 2003, 68, 8859.
[12] Charupant, K.; Suwanborirux, K.; Amnuoypol, S.; Saito, E.; Kubo, A.; Saito, N. Chem. Pharm. Bull. 2007, 55, 81.
[13] Fontana,A.; Cavaliere, P.; Wahidulla, S.; Naik, C. G.; Cimino, G. Tetrahedron 2000, 56, 7305.
[14] (a) Saito, N.; Tanaka, C.; Koizumi, Y.; Suwanborirux, K.; Amnuoypol, S.; Pummangura, S.; Kubo, A. Tetrahedron 2004, 60, 3873. (b) Charupant, K.; Daikuhara, N.; Saito, E.; Amnuoypol, S.; Suwanborirux, K.; Owa, T.; Saito, N. Bioorg. Med. Chem. 2009, 17, 4548. (c) Liu, W.; Liao, X.; Dong, W.; Yan, Z.; Wang, N.; Liu, Z. Tetrahedron 2012, 68, 2759.
[15] Fukuyama, T.; Linton, S. D.; Tun, M. M. Tetrahedron Lett. 1990, 31, 5989.
[16] Godfrey, I. M.; Sargent, M. V.; Elix, J. A. J. Chem. Soc., Perkin Trans. 1 1974, 1353.
[17] Davidson, B. S. Tetrahedron Lett. 1992, 33, 3721.
[18] Yokoya, M.; Shinada-Fujino, K.; Saito, N. Tetrahedron Lett. 2011, 52, 2446.
[19] Yokoya, M.; Shinada-Fujino, K.; Yoshida, S.; Mimura, M.; Takada, H.; Saito, N. Tetrahedron 2012, 68, 4166.
[20] (a) Parameswaran, P. S.; Naik, C. G.; Kamat, S. Y.; Pramanik, B. N. Indian J. Chem., 1998, 37B, 1258. (b) Pettit, G. R.; Knight, J. C.; Collins, J. C.; Herald, D. L.; Pettit, R. K.; Boyd, M. R.; Young, V. G. J. Nat. Prod. 2000, 63, 793. (c) Saito, N.; Sakai, H.; Suwanborirux, K.; Pummangura, S.; Kubo, A. Heterocycles 2001, 55, 21.
[21] (a) Yokoya, M.; Ito, H.; Saito, N. Chem. Pharm. Bull. 2011, 59, 787. (b) Yokoya, M.; Ito, H.; Saito, N. Tetrahedron 2011, 67, 9185.
[22] Matsuo, K.; Okumura, M.; Tanaka, T. Chem. Pharm. Bull. 1982, 30, 4170.
[23] Kubo A.; Saito N.; Yamato H.; Kawakami Y.; Chem. Pharm. Bull. 1987, 35, 2525.
[24] Lane, J. W.; Chen, Y.; Williams, R. M. J. Am. Chem. Soc. 2005, 127, 12684.
[25] Jin, W.; Williams, R. M. Tetrahedron Lett. 2003, 44, 4635.
[26] Fukuyama, T.; Sachleben, R. A. J. Am. Chem. Soc. 1982, 104, 4957.
[27] (a) Magnus, P.; Matthews, K. S. J. Am. Chem. Soc. 2005, 127, 12476. (b) Magnus, P.; Matthews, K. S. Tetrahedron 2012, 68, 6343.
[28] (a) Rinehart, K. L.; Holt, T. G.; Fregeau, N. L.; Stroh, J. G.; Kieffer, P. A.; Sun, F.; Li, L. H.; Martin, D. G. J. Org. Chem. 1990, 55, 4512. (b) Rinehart, K. L.; Holt, T. G.; Fregeau, N. L.; Stroh, J. G.; Kieffer, P. A.; Sun, F.; Li, L. H.; Martin, D. G. J. Org. Chem. 1991, 56, 1676.
[29] Chan, C.; Heid, R.; Zheng, S.; Guo, J.; Zhou, B.; Furuuchi, T.; Danishefsky, S. J. J. Am. Chem. Soc. 2005, 127, 4596.
[30] Sinhababu, A. K.; Ghosh, A. K.; Borchardt, R. T. J. Med. Chem. 1985, 28, 1273.
[31] Vincent, G.; Williams, R. M. Angew. Chem. Int. Ed. 2007, 46, 1517.
[32] Evans, D. A.; Sjogren, E. B. Tetrahedron Lett. 1985, 26, 3783.
[33] Chen, X.; Zhu, J. Angew. Chem. Int. Ed. 2007, 46, 3962.
[34] Liao, X. W.; Liu, W.; Dong, W. F.; Guan, B. H.; Chen, S. Z.; Liu, Z. Z. Tetrahedron 2009, 65, 5709.
[35] Wu, Y.-C.; Zhu, J. Org. Lett. 2009, 11, 5558.
[36] Suwanborirux, K.; Amnuoypol, S.; Plubrukarn, A.; Pummangura, S.; Kubo, A.; Tanaka,C.; Saito, N. J. Nat. Prod. 2003, 66, 1441.
[37] (a) Chen, X.; Chen, J.; Paolis, M. D.; Zhu, J. J. Org. Chem. 2005, 70, 4397. (b) Vincent, G.; Lane, J. W.; Williams, R. M. Tetrahedron Lett. 2007, 48, 3719. (c) Liao, X. W.; Dong, W. F.; Liu, W.; Guan, B. H.; Liu, Z. Z. J. Heterocycl. Chem. 2011, 48, 414.
[38] (a) Myers, A. G.; Schnider, P.; Kwon, S.; Kung, D. W. J. Org. Chem. 1999, 64, 3322. (b) Obika, S.; Yasui, Y.; Yanada, R.; Takemoto, Y. J. Org. Chem. 2008, 73, 5206.
[39] Chen, R.; Liu, H.; Chen, X. J. Nat. Prod. 2013, 76, 1789.
[40] (a) Chen, R.; Zhu, D.; Hu, Z.; Zheng, Z.; Chen, X. Tetrahedron: Asymmetry 2010, 21, 39. (b) Chen, R.; Liu, H.; Liu, X.; Chen, X. Tetrahedron 2013, 69, 3565.
[41] Tatsukawa, M.; Punzalan, L. L. C.; Magpantay, H. D.S.; Villaseñor, I. M.; Concepcion, G. P.; Suwanborirux, K.; Yokoya, M.; Saito, N. Tetrahedron 2012, 68, 7422.
[42] Liu, H.; Chen, R.; Chen, X. Org. Biomol. Chem. 2014, 12, 1633.
[43] (a) Liu, Z.-Z.; Wang, Y.; Tang, Y.-F.; Chen, S.-Z.; Chen, X.-G.; Li, H.-Y. Bioorg. Med. Chem. Lett. 2006, 16, 1282. (b) Otrín, I.; González, J. F.; de la Cuesta, E.; Manguan-García, C.; Perona, R.; Avendaño, C.; Bioorg. Med. Chem. 2008, 16, 9065. (c) Otrín, I.; González, J. F.; de la Cuesta, E.; Avendaño, C.; Tetrahedron 2009, 65, 2201. (d) Otrín, I.; González, J. F.; de la Cuesta, E.; Avendaño, C.; Tetrahedron 2009, 65, 9944. (e) Pan, L.; Chen, R.; Ni, D.; Xia, L.; Chen, X. Synlett 2013, 241. (f) Nakai, K.; Yokoya, M.; Saito, N. Chem. Pharm. Bull. 2013, 61, 853. (g) Nakai, K.; Kubo, K.; Yokoya, M.; Saito, N. Tetrahedron 2014, 70, 6529.

Renieramycin类生物碱的合成研究进展