Synthesis of β-Amino Carbonyl Compounds and Its Application: Total Synthesis of (+)-Sedridine
- Corresponding author: Sun Xingwen, sunxingwen@fudan.edu.cn
Citation:
Sun Kai, Sun Xingwen, Lin Guoqiang. Synthesis of β-Amino Carbonyl Compounds and Its Application: Total Synthesis of (+)-Sedridine[J]. Chinese Journal of Organic Chemistry,
;2018, 38(1): 131-137.
doi:
10.6023/cjoc201710022
Kenchappa, R.; Bodke, Y. D.; Peethambar, S. K.; Telkar, S.; Bhovi, V. K. Med. Chem. Res. 2013, 22, 4787.
doi: 10.1007/s00044-013-0494-7
Liu, C.-Y.; Huang, C.-J. Langmuir 2016, 32, 5019.
doi: 10.1021/acs.langmuir.6b00990
Raundal, P.; Watpade, R.; Patil, P.; Aher, J. Pharma Chem. 2016, 8, 27.
Sankappa Rai, U.; Isloor, A. M.; Shetty, P.; Isloor, N.; Malladi, S.; Fun, H.-K. Eur. J. Med. Chem. 2010, 45, 6090.
doi: 10.1016/j.ejmech.2010.09.015
Steer, D. L.; Lew, R. A.; Perlmutter, P.; Smith, A. I.; Aguilar, M.-I. Curr. Med. Chem. 2002, 9, 811.
doi: 10.2174/0929867024606759
Seebach, D.; Beck, A. K.; Bierbaum, D. J. Chem. Biodiversity 2004, 1, 1111.
doi: 10.1002/(ISSN)1612-1880
Kuhl, A.; Hahn, M. G.; Dumic, M.; Mittendorf, J. Amino Acids 2005, 29, 89.
doi: 10.1007/s00726-005-0212-y
Seebach, D.; Gardiner, J. Acc. Chem. Res. 2008, 41, 1366.
doi: 10.1021/ar700263g
Cabrele, C.; Martinek, T. A.; Reiser, O.; Berlicki, L. J. Med. Chem. 2014, 57, 9718.
doi: 10.1021/jm5010896
Bhadury, P. S.; Yang, S.; Song, B.-A. Curr. Org. Synth. 2012, 9, 695.
doi: 10.2174/157017912803251783
Gundogdu, O.; Turhan, P.; Kose, A.; Altundas, R.; Kara, Y. Tetrahedron: Asymmetry 2017, 28, 1163.
doi: 10.1016/j.tetasy.2017.08.009
Kawanaka, Y.; Phillips, E. M.; Scheidt, K. A. J. Am. Chem. Soc. 2009, 131, 18028.
doi: 10.1021/ja9094044
Hu, Q.; Chen, J.; Zhang, Z.; Liu, Y.; Zhang, W. Org. Lett. 2016, 18, 1290.
doi: 10.1021/acs.orglett.6b00212
Tang, S.; He, J.; Sun, Y.; He, L.; She, X. J. Org. Chem. 2010, 75, 1961.
doi: 10.1021/jo1000065
Zhang, D.; Chen, X.; Chi, J.; Feng, J.; Wu, Q.; Zhu, D. ACS Catal. 2015, 5, 2452.
doi: 10.1021/acscatal.5b00226
Alanthadka, A.; Devi, E. S.; Selvi, A. T.; Nagarajan, S.; Sridharan, V.; Maheswari, C. U. Adv. Synth. Catal. 2017, 359, 2369.
doi: 10.1002/adsc.v359.14
Chan, J. Z.; Yao, W.; Hastings, B. T.; Lok, C. K.; Wasa, M. Angew. Chem., Int. Ed. 2016, 55, 13877.
doi: 10.1002/anie.201608583
Kabiri Esfahani, F.; Zareyee, D.; Shokuhi Rad, A.; Taher-Bahrami, S. Appl. Organomet. Chem. 2017, Ahead of Print.
Li, X.; Li, Y.; Shang, H. Org. Biomol. Chem. 2016, 14, 6457.
doi: 10.1039/C6OB01084A
Li, Y.; Li, X.; Shang, H.; Chen, X.; Ren, X. J. Org. Chem. 2016, 81, 9858.
doi: 10.1021/acs.joc.6b01979
Qian, H.; Kai, W.; Zhen, J. Lett. Org. Chem. 2016, 13, 143.
doi: 10.2174/1570178613666151207195530
Sarma, P.; Saikia, S.; Borah, R. Synth. Commun. 2015, 45, 2810.
doi: 10.1080/00397911.2015.1105983
Cihalova, S.; Remes, M.; Cisarova, I.; Vesely, J. Eur. J. Org. Chem. 2009, 6277.
Matsui, K.; Takizawa, S.; Sasai, H. J. Am. Chem. Soc. 2005, 127, 3680.
doi: 10.1021/ja0500254
Mazzotta, S.; Gramigna, L.; Bernardi, L.; Ricci, A. Org. Process Res. Dev. 2010, 14, 687.
doi: 10.1021/op1000308
Sun, S.; Zhang, Q.; Liu, Q.; Kang, J.; Yin, Y.; Li, D.; Dong, D. Tetrahedron Lett. 2005, 46, 6271.
doi: 10.1016/j.tetlet.2005.07.047
Utsumi, N.; Zhang, H.; Tanaka, F.; Barbas Ⅲ, C. F. Angew. Chem., Int. Ed. 2007, 46, 1878.
doi: 10.1002/(ISSN)1521-3773
Xu, Y.-M.; Shi, M. J. Org. Chem. 2004, 69, 417.
doi: 10.1021/jo035103p
Congdon, E. A.; Nolin, K. A. Catal. Commun. 2016, 79, 35.
doi: 10.1016/j.catcom.2016.02.003
Huang, C.; Yin, Y.; Guo, J.; Wang, J.; Fan, B.; Yang, L. RSC Adv. 2014, 4, 10188.
doi: 10.1039/c3ra46789a
Kim, S.; Kang, S.; Kim, G.; Lee, Y. J. Org. Chem. 2016, 81, 4048.
doi: 10.1021/acs.joc.6b00341
Panwar, V.; Ray, S. S.; Jain, S. L. Tetrahedron Lett. 2016, 57, 5026.
doi: 10.1016/j.tetlet.2016.09.093
Shobeiri, Z.; Pourayoubi, M.; Heydari, A.; Percino, T. M.; Ramirez, M. A. L. C. R. Chim. 2011, 14, 597.
doi: 10.1016/j.crci.2011.03.002
Davis, F. A.; Nolt, M. B.; Wu, Y.; Prasad, K. R.; Li, D.; Yang, B.; Bowen, K.; Lee, S. H.; Eardley, J. H. J. Org. Chem. 2005, 70, 2184.
doi: 10.1021/jo0402780
Davis, F. A.; Prasad, K. R.; Nolt, M. B.; Wu, Y. Org. Lett. 2003, 5, 925.
doi: 10.1021/ol034119z
Zhang, X.; Li, P.; Chang, L.; Yong, W.; Li, J.; Pan, X.; Zhu, X.; Rao, W. Adv. Synth. Catal. 2017, Ahead of Print (DOI:10.1002/adsc.201700838).
doi: 10.1002/adsc.201700838)
Chen, X.-Y.; Sun, L.-S.; Gao, X.; Sun, X.-W. J. Chem. Educ. 2015, 92, 714.
doi: 10.1021/ed500292q
Guo, T.; Song, R.; Yuan, B.-H.; Chen, X.-Y.; Sun, X.-W.; Lin, G.-Q. Chem. Commun. (Cambridge, U. K.) 2013, 49, 5402.
Lin, G.-Q.; Xu, M.-H.; Zhong, Y.-W.; Sun, X.-W. Acc. Chem. Res. 2008, 41, 831.
doi: 10.1021/ar7002623
Liu, M.; Shen, A.; Sun, X.-W.; Deng, F.; Xu, M.-H.; Lin, G.-Q. Chem. Commun. (Cambridge, U. K.) 2010, 46, 8460.
doi: 10.1039/c0cc03230a
Sun, X.-W.; Liu, M.; Xu, M.-H.; Lin, G.-Q. Org. Lett. 2008, 10, 1259.
doi: 10.1021/ol8001514
Sun, X.-W.; Xu, M.-H.; Lin, G.-Q. Org. Lett. 2006, 8, 4979.
doi: 10.1021/ol062216x
Yuan, B.-H.; Zhang, Z.-C.; Liu, W.-J.; Sun, X.-W. Tetrahedron Lett. 2016, 57, 2147.
doi: 10.1016/j.tetlet.2016.03.103
Zhao, Y.-S.; Liu, Q.; Tian, P.; Tao, J.-C.; Lin, G.-Q. Org. Biomol. Chem. 2015, 13, 4174.
doi: 10.1039/C5OB00322A
Itoh, T.; Nishimura, K.; Nagata, K.; Yokoya, M. Synlett 2006, 2207.
Littler, B. J.; Gallagher, T.; Boddy, I. K.; Riordan, P. D. Synlett 1997, 22.
Louis, C.; Hootele, C. Tetrahedron: Asymmetry 1995, 6, 2149.
doi: 10.1016/0957-4166(95)00287-Y
Murahashi, S.; Imada, Y.; Kohno, M.; Kawakami, T. Synlett 1993, 395.
Nagata, K.; Nishimura, K.; Yokoya, M.; Itoh, T. Heterocycles 2006, 70, 335.
doi: 10.3987/COM-06-S(W)29
Nuguri, S.; Eppakayala, L.; Vuppula, N. K.; Kottapalli Rajasekhara, P. Int. J. Chem. Anal. Sci. 2013, 4, 131.
doi: 10.1016/j.ijcas.2013.07.004
Ren, H.; Wulff, W. D. Org. Lett. 2013, 15, 242.
doi: 10.1021/ol302769r
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Reagents and conditions: (a) TsCl, Et3N, DMAP, 77%; (b) TEMPO, NaClO, 96%; (c) (S)-(-)-tert-Butylsulfinamide, AmberlystTM-15 H2O, 97%; (d) In, allyl bromide, 97%; (e) NaH, THF, 83%; (f) HCl, MeOH, (Boc)2O, NaOH, 90%; (g) Pd(AcO)2 (20 mol%), CuCl (1 equiv.), O2 (101 kPa), r.t., MeCN and H2O (18 mL, V:V=7:1), 60 h, 89%; (h) LiEt3BH, DCM, 73%; (i) HCl, MeOH, 94%.