Synthesis of β-Amino Carbonyl Compounds and Its Application: Total Synthesis of (+)-Sedridine

doi:10.6023/cjoc201710022

Chin. J. Org. Chem. ›› 2018, Vol. 38 ›› Issue (1): 131-137.DOI: 10.6023/cjoc201710022 Previous Articles Next Articles

Special Issue: 庆祝吴养洁院士九十华诞专辑

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β-氨基羰基化合物合成研究及其应用:(+)-Sedridine的全合成

孙凯^a, 孙兴文^a, 林国强^a,b

a 复旦大学化学系上海 200433;
b 中国科学院上海有机化学研究所上海 200032

收稿日期:2017-10-20 修回日期:2017-10-31 发布日期:2017-11-03
通讯作者: 孙兴文 E-mail:sunxingwen@fudan.edu.cn
基金资助:
国家自然科学基金（No.20802009）资助项目.

Synthesis of β-Amino Carbonyl Compounds and Its Application: Total Synthesis of (+)-Sedridine

Sun Kai^a, Sun Xingwen^a, Lin Guoqiang^a,b

a Department of Chemistry, Fudan University, Shanghai 200433;
b Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032

Received:2017-10-20 Revised:2017-10-31 Published:2017-11-03
Contact: 10.6023/cjoc201710022 E-mail:sunxingwen@fudan.edu.cn
Supported by:
Project supported by the National Natural Science Foundation of China (No. 20802009).

1. Synthesis of β-Amino Carbonyl Compounds and Its Application: Total Synthesis of (+)-Sedridine.PDF(6531KB)

Abstract

β-Amino-carbonyl fragments are important structures of many bioactive molecules and pharmaceuticals and critical synthetic blocks which can be easily converted into other structures and compounds. A novel method for preparing β-amino-carbonyl compounds with oxygen as an oxidant, palladium acetate and cuprous chloride as catalysts was reported. The chiral high allyl amine compounds can be converted into corresponding β-amino carbonyl compounds with moderate to good yield, good substrate scope, and tolerance of chiral centers. Natural product (+)-sedridine was synthesized with 32% yield.

Key words: β-amino carbonyl compound, chiral high allyl amine, Wacker reaction, (+)-sedridine

Cite this article

Sun Kai, Sun Xingwen, Lin Guoqiang. Synthesis of β-Amino Carbonyl Compounds and Its Application: Total Synthesis of (+)-Sedridine[J]. Chin. J. Org. Chem., 2018, 38(1): 131-137.

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[1] Kenchappa, R.; Bodke, Y. D.; Peethambar, S. K.; Telkar, S.; Bhovi, V. K. Med. Chem. Res. 2013, 22, 4787.
[2] Liu, C.-Y.; Huang, C.-J. Langmuir 2016, 32, 5019.
[3] Raundal, P.; Watpade, R.; Patil, P.; Aher, J. Pharma Chem. 2016, 8, 27.
[4] Sankappa Rai, U.; Isloor, A. M.; Shetty, P.; Isloor, N.; Malladi, S.; Fun, H.-K. Eur. J. Med. Chem. 2010, 45, 6090.
[5] Steer, D. L.; Lew, R. A.; Perlmutter, P.; Smith, A. I.; Aguilar, M.-I. Curr. Med. Chem. 2002, 9, 811.
[6] Seebach, D.; Beck, A. K.; Bierbaum, D. J. Chem. Biodiversity 2004, 1, 1111.
[7] Kuhl, A.; Hahn, M. G.; Dumic, M.; Mittendorf, J. Amino Acids 2005, 29, 89.
[8] Seebach, D.; Gardiner, J. Acc. Chem. Res. 2008, 41, 1366.
[9] Cabrele, C.; Martinek, T. A.; Reiser, O.; Berlicki, L. J. Med. Chem. 2014, 57, 9718.
[10] Bhadury, P. S.; Yang, S.; Song, B.-A. Curr. Org. Synth. 2012, 9, 695.
[11] Gundogdu, O.; Turhan, P.; Kose, A.; Altundas, R.; Kara, Y. Tetrahedron: Asymmetry 2017, 28, 1163.
[12] Kawanaka, Y.; Phillips, E. M.; Scheidt, K. A. J. Am. Chem. Soc. 2009, 131, 18028.
[13] Hu, Q.; Chen, J.; Zhang, Z.; Liu, Y.; Zhang, W. Org. Lett. 2016, 18, 1290.
[14] Tang, S.; He, J.; Sun, Y.; He, L.; She, X. J. Org. Chem. 2010, 75, 1961.
[15] Zhang, D.; Chen, X.; Chi, J.; Feng, J.; Wu, Q.; Zhu, D. ACS Catal. 2015, 5, 2452.
[16] Alanthadka, A.; Devi, E. S.; Selvi, A. T.; Nagarajan, S.; Sridharan, V.; Maheswari, C. U. Adv. Synth. Catal. 2017, 359, 2369.
[17] Chan, J. Z.; Yao, W.; Hastings, B. T.; Lok, C. K.; Wasa, M. Angew. Chem., Int. Ed. 2016, 55, 13877.
[18] Kabiri Esfahani, F.; Zareyee, D.; Shokuhi Rad, A.; Taher-Bahrami, S. Appl. Organomet. Chem. 2017, Ahead of Print.
[19] Li, X.; Li, Y.; Shang, H. Org. Biomol. Chem. 2016, 14, 6457.
[20] Li, Y.; Li, X.; Shang, H.; Chen, X.; Ren, X. J. Org. Chem. 2016, 81, 9858.
[21] Qian, H.; Kai, W.; Zhen, J. Lett. Org. Chem. 2016, 13, 143.
[22] Sarma, P.; Saikia, S.; Borah, R. Synth. Commun. 2015, 45, 2810.
[23] Cihalova, S.; Remes, M.; Cisarova, I.; Vesely, J. Eur. J. Org. Chem. 2009, 6277.
[24] Matsui, K.; Takizawa, S.; Sasai, H. J. Am. Chem. Soc. 2005, 127, 3680.
[25] Mazzotta, S.; Gramigna, L.; Bernardi, L.; Ricci, A. Org. Process Res. Dev. 2010, 14, 687.
[26] Sun, S.; Zhang, Q.; Liu, Q.; Kang, J.; Yin, Y.; Li, D.; Dong, D. Tetrahedron Lett. 2005, 46, 6271.
[27] Utsumi, N.; Zhang, H.; Tanaka, F.; Barbas Ⅲ, C. F. Angew. Chem., Int. Ed. 2007, 46, 1878.
[28] Xu, Y.-M.; Shi, M. J. Org. Chem. 2004, 69, 417.
[29] Congdon, E. A.; Nolin, K. A. Catal. Commun. 2016, 79, 35.
[30] Huang, C.; Yin, Y.; Guo, J.; Wang, J.; Fan, B.; Yang, L. RSC Adv. 2014, 4, 10188.
[31] Kim, S.; Kang, S.; Kim, G.; Lee, Y. J. Org. Chem. 2016, 81, 4048.
[32] Panwar, V.; Ray, S. S.; Jain, S. L. Tetrahedron Lett. 2016, 57, 5026.
[33] Shobeiri, Z.; Pourayoubi, M.; Heydari, A.; Percino, T. M.; Ramirez, M. A. L. C. R. Chim. 2011, 14, 597.
[34] 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.
[35] Davis, F. A.; Prasad, K. R.; Nolt, M. B.; Wu, Y. Org. Lett. 2003, 5, 925.
[36] 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).
[37] Chen, X.-Y.; Sun, L.-S.; Gao, X.; Sun, X.-W. J. Chem. Educ. 2015, 92, 714.
[38] Guo, T.; Song, R.; Yuan, B.-H.; Chen, X.-Y.; Sun, X.-W.; Lin, G.-Q. Chem. Commun. (Cambridge, U. K.) 2013, 49, 5402.
[39] Lin, G.-Q.; Xu, M.-H.; Zhong, Y.-W.; Sun, X.-W. Acc. Chem. Res. 2008, 41, 831.
[40] Liu, M.; Shen, A.; Sun, X.-W.; Deng, F.; Xu, M.-H.; Lin, G.-Q. Chem. Commun. (Cambridge, U. K.) 2010, 46, 8460.
[41] Sun, X.-W.; Liu, M.; Xu, M.-H.; Lin, G.-Q. Org. Lett. 2008, 10, 1259.
[42] Sun, X.-W.; Xu, M.-H.; Lin, G.-Q. Org. Lett. 2006, 8, 4979.
[43] Yuan, B.-H.; Zhang, Z.-C.; Liu, W.-J.; Sun, X.-W. Tetrahedron Lett. 2016, 57, 2147.
[44] Zhao, Y.-S.; Liu, Q.; Tian, P.; Tao, J.-C.; Lin, G.-Q. Org. Biomol. Chem. 2015, 13, 4174.
[45] Itoh, T.; Nishimura, K.; Nagata, K.; Yokoya, M. Synlett 2006, 2207.
[46] Littler, B. J.; Gallagher, T.; Boddy, I. K.; Riordan, P. D. Synlett 1997, 22.
[47] Louis, C.; Hootele, C. Tetrahedron: Asymmetry 1995, 6, 2149.
[48] Murahashi, S.; Imada, Y.; Kohno, M.; Kawakami, T. Synlett 1993, 395.
[49] Nagata, K.; Nishimura, K.; Yokoya, M.; Itoh, T. Heterocycles 2006, 70, 335.
[50] Nuguri, S.; Eppakayala, L.; Vuppula, N. K.; Kottapalli Rajasekhara, P. Int. J. Chem. Anal. Sci. 2013, 4, 131.
[51] Ren, H.; Wulff, W. D. Org. Lett. 2013, 15, 242.

β-氨基羰基化合物合成研究及其应用:(+)-Sedridine的全合成

Synthesis of β-Amino Carbonyl Compounds and Its Application: Total Synthesis of (+)-Sedridine

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