Applications of Transition Metal Catalyzed Coupling Reactions in the Synthesis of C-Glycosides
- Corresponding author: Sun Jiansong, jssun@jxnu.edu.cn
Citation:
Liao Jinxi, Liu Hui, Sun Jiansong. Applications of Transition Metal Catalyzed Coupling Reactions in the Synthesis of C-Glycosides[J]. Chinese Journal of Organic Chemistry,
;2017, 37(6): 1382-1391.
doi:
10.6023/cjoc201612031
Zou, W. Curr. Top. Med. Chem. 2005, 5, 1363.
doi: 10.2174/156802605774642999
Hultin, P. G. Curr. Top. Med. Chem. 2005, 5, 1299.
doi: 10.2174/156802605774643015
(a) Cao, X.; Tian, Y.; Zhang, T.; Li, X.; Ito, Y. J. Chromatogr. A 1999, 855, 709.
(b) Nomura, S.; Sakamaki, S.; Hongu, M.; Kawanishi, E.; Koga, Y.; Sakamoto, T.; Yamamoto, Y.; Ueta, K.; Kimata, H.; Nakayama, K.; Tsuda-Tsukimoto, M. J. Med. Chem. 2010, 53, 6355.
Moore, R. E.; Scheuer, P. J. Science 1971, 172, 495.
doi: 10.1126/science.172.3982.495
(a) De Clercq, E. J. Med. Chem. 2016, 59, 2301.
(b) Lalitha, K.; Muthusamy, K.; Prasad, Y. S.; Vemula, P. K.; Nagarajan, S. Carbohydr. Res. 2015, 402, 158.
(c) Yuan, X. J.; Linhardt, R. J. Curr. Top. Med. Chem. 2005, 5, 1393.
(d) Du, Y.; Linhardt, R. J.; Vlahov, I. R. Tetrahedron 1998, 54, 9913.
(e) Lee, D. Y. W.; He, M. S. Curr. Top. Med. Chem. 2005, 5, 1333.
(f) Wellington, K. W.; Benner, S. A. Nucleosides Nucleotides Nucleic Acids 2006, 25, 1309.
(g) Li, X.; Zhu, J. Eur. J. Org. Chem. 2016, 2016, 4724.
Bergstrom, D. E.; Ruth, J. L. J. Am. Chem. Soc. 1976, 98, 1587.
doi: 10.1021/ja00422a056
Arai, I.; Daves, G. D. J. Am. Chem. Soc. 1978, 100, 287.
doi: 10.1021/ja00469a051
Daves, G. D. Acc. Chem. Res. 1990, 23, 201.
doi: 10.1021/ar00174a006
Cheng, J. C. Y.; Daves, G. D. J. Org. Chem. 1987, 52, 3083.
doi: 10.1021/jo00390a022
Ramnauth, J.; Poulin, O.; Rakhit, S.; Maddaford, S. P. Org. Lett. 2001, 3, 2013.
doi: 10.1021/ol010070q
Beletskaya, I. P.; Cheprakov, A. V. Chem. Rev. 2000, 100, 3009.
doi: 10.1021/cr9903048
Xiong, D. C.; Zhang, L. H.; Ye, X. S. Org. Lett. 2009, 11, 1709.
doi: 10.1021/ol900273d
Li, H. H.; Ye, X. S. Org. Biomol. Chem. 2009, 7, 3855.
doi: 10.1039/b909248j
Kusunuru, A. K.; Jaladanki, C. K.; Tatina, M. B.; Bharatam, P. V.; Mukherjee, D. Org. Lett. 2015, 17, 3742.
doi: 10.1021/acs.orglett.5b01722
Lei, M.; Gao, L.; Yang, J.-S. Tetrahedron Lett. 2009, 50, 5135.
doi: 10.1016/j.tetlet.2009.06.116
Bai, Y.; Leow, M.; Zeng, J.; Liu, X. W. Org. Lett. 2011, 13, 5648.
doi: 10.1021/ol202368n
Dunkerton, L. V.; Euske, J. M.; Serino, A. J. Carbohydr. Res. 1987, 171, 89.
doi: 10.1016/S0008-6215(00)90881-4
Brakta, M.; Lhoste, P.; Sinou, D. J. Org. Chem. 1989, 54, 1890.
doi: 10.1021/jo00269a026
Friesen, R. W.; Sturino, C. F. J. Org. Chem. 1990, 55, 2572.
doi: 10.1021/jo00296a005
Lehmann, U.; Awasthi, S.; Minehan, T. Org. Lett. 2003, 5, 2405.
doi: 10.1021/ol0345428
Tius, M. A.; Gomez-Galeno, J.; Gu, X. Q.; Zaidi, J. H. J. Am. Chem. Soc. 1991, 113, 5775.
doi: 10.1021/ja00015a035
Ousmer, M.; Boucard, V.; Lubin-Germain, N.; Uziel, J.; Augé, J. Eur. J. Org. Chem. 2006, 1216.
Koester, D. C.; Leibeling, M.; Neufeld, R.; Werz, D. B. Org. Lett. 2010, 12, 3934.
doi: 10.1021/ol101625p
Schmidt, R. R.; Preuss, R.; Betz, R. Tetrahedron Lett. 1987, 28, 6591.
doi: 10.1016/S0040-4039(00)96921-1
Koester, D. C.; Kriemen, E.; Werz, D. B. Angew. Chem., Int. Ed. 2013, 52, 2985.
doi: 10.1002/anie.201209697
Belosludtsev, Y. Y.; Bhatt, R. K.; Falck, J. R. Tetrahedron Lett. 1995, 36, 5881.
doi: 10.1016/00404-0399(50)1183I-
Zhu, F.; Rourke, M. J.; Yang, T. Y.; Rodriguez, J.; Walczak, M. A. J. Am. Chem. Soc. 2016, 138, 12049.
doi: 10.1021/jacs.6b07891
Jeanneret, V.; Meerpoel, L.; Vogel, P. Tetrahedron Lett. 1997, 38, 543.
doi: 10.1016/S0040-4039(96)02367-2
Potuzak, J. S.; Tan, D. S. Tetrahedron Lett. 2004, 45, 1797.
doi: 10.1016/j.tetlet.2003.12.006
(a) Lyons, T. W.; Sanford, M. S. Chem. Rev. 2010, 110, 1147.
(b) Liu, C.; Zhang, H.; Shi, W.; Lei, A. Chem. Rev. 2011, 111, 1780.
Liu, M.; Niu, Y.; Wu, Y. F.; Ye, X. S. Org. Lett. 2016, 18, 1836.
doi: 10.1021/acs.orglett.6b00566
Myers, A. G.; Tanaka, D.; Mannion, M. R. J. Am. Chem. Soc. 2002, 124, 11250.
doi: 10.1021/ja027523m
Rodriguez, N.; Goossen, L. J. Chem. Soc. Rev. 2011, 40, 5030.
doi: 10.1039/c1cs15093f
Xiang, S.; Cai, S.; Zeng, J.; Liu, X. W. Org. Lett. 2011, 13, 4608.
doi: 10.1021/ol201820m
Zeng, J.; Ma, J.; Xiang, S.; Cai, S.; Liu, X. W. Angew. Chem., Int. Ed. 2013, 52, 5134.
doi: 10.1002/anie.201210266
Kito, K.; Ookura, R.; Yoshida, S.; Namikoshi, M.; Ooi, T.; Kusumi, T. Org. Lett. 2008, 10, 225.
doi: 10.1021/ol702598q
Ma, J.; Xiang, S.; Jiang, H.; Liu, X.-W. Eur. J. Org. Chem. 2015, 2015, 949.
doi: 10.1002/ejoc.v2015.5
Kusunuru, A. K.; Yousuf, S. K.; Tatina, M.; Mukherjee, D. Eur. J. Org. Chem. 2015, 2015, 459.
doi: 10.1002/ejoc.201403195
Bai, Y.; Kim, L. M. H.; Liao, H.; Liu, X.-W. J. Org. Chem. 2013, 78, 8821.
doi: 10.1021/jo401032r
Trost, B. M.; McEachern, E. J.; Toste, F. D. J. Am. Chem. Soc. 1998, 120, 12702.
doi: 10.1021/ja983238k
Nicolaou, K. C.; Sato, M.; Miller, N. D.; Gunzner, J. L.; Renaud, J.; Untersteller, E. Angew. Chem., Int. Ed. 1996, 35, 889.
doi: 10.1002/(ISSN)1521-3773
Bai, Y.; Leng, W. L.; Li, Y.; Liu, X. W. Chem. Commun. (Camb.) 2014, 50, 13391.
doi: 10.1039/C4CC06111J
Readman, S. K.; Marsden, S. P.; Hodgson, A. Synlett 2000, 1628.
(a) Adlington, R. M.; Baldwin, J. E.; Basak, A.; Kozyrod, R. P. J. Chem. Soc., Chem. Commun. 1983, 944.
(b) Dunach, E.; Esteves, A. P.; Freitas, A. M.; Medeiros, M. J.; Olivero, S. Tetrahedron Lett. 1999, 40, 8693.
Gong, H. G.; Sinisi, R.; Gagne, M. R. J. Am. Chem. Soc. 2007, 129, 1908.
doi: 10.1021/ja068950t
Gong, H. G.; Gagne, M. R. J. Am. Chem. Soc. 2008, 130, 12177.
doi: 10.1021/ja8041564
Gong, H. G.; Andrews, R. S.; Zuccarello, J. L.; Lee, S. J.; Gagne, M. R. Org. Lett. 2009, 11, 879.
doi: 10.1021/ol8028737
(a) Zhao, C.; Jia, X.; Wang, X.; Gong, H. J. Am. Chem. Soc. 2014, 136, 17645.
(b) Jia, X.; Zhang, X.; Qian, Q.; Gong, H. Chem. Commun. (Camb.) 2015, 51, 10302.
Zheng, M.; Xue, W.; Xue, T.; Gong, H. Org. Lett. 2016, 18, 6152.
doi: 10.1021/acs.orglett.6b03158
Liu, C. F.; Xiong, D. C.; Ye, X. S. J. Org. Chem. 2014, 79, 4676.
doi: 10.1021/jo500730y
Nicolas, L.; Angibaud, P.; Stansfield, I.; Bonnet, P.; Meerpoel, L.; Reymond, S.; Cossy, J. Angew. Chem. 2012, 124, 11263.
doi: 10.1002/ange.201204786
Juhász, Z.; Micskei, K.; Gál, E.; Somsák, L. Tetrahedron Lett. 2007, 48, 7351.
doi: 10.1016/j.tetlet.2007.08.019
Andrews, R. S.; Becker, J. J.; Gagné, M. R. Angew. Chem. 2010, 122, 7432.
doi: 10.1002/ange.v122:40
Andrews, R. S.; Becker, J. J.; Gagne, M. R. Org. Lett. 2011, 13, 2406.
doi: 10.1021/ol200644w
Andrews, R. S.; Becker, J. J.; Gagne, M. R. Angew. Chem., Int. Ed. 2012, 51, 4140.
doi: 10.1002/anie.201200593
Ramnauth, J.; Poulin, O.; Bratovanov, S. S.; Rakhit, S.; Maddaford, S. P. Org. Lett. 2001, 3, 2571.
doi: 10.1021/ol016245d
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