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2013 , Vol. 33 >Issue 9: 1932 - 1938

DOI: https://doi.org/10.6023/cjoc201305051

研究论文

D-(R)-酪氨酸的不对称催化氢化合成及其在药物合成中的应用

  • 余坤矫 ,
  • 张振锋 ,
  • 霍小红 ,
  • 王兴广 ,
  • 刘德龙 ,
  • 张万斌
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  • a 上海交通大学药学院 上海 200240;
    b 上海交通大学化学化工学院 上海 200240

收稿日期: 2013-05-30

  修回日期: 2013-06-07

  网络出版日期: 2013-06-21

基金资助

上海市经济与信息化委员会基金(No. 12CH-02)资助项目

收起

Synthesis of D-(R)-Tyrosine by Catalytic Asymmetric Hydrogenation and Its Practical Application

  • Yu Kunjiao ,
  • Zhang Zhenfeng ,
  • Huo Xiaohong ,
  • Wang Xingguang ,
  • Liu Delong ,
  • Zhang Wanbin
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  • a School of Pharmacy, Shanghai Jiao Tong University, Shanghai 200240;
    b School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, Shanghai 200240

Received date: 2013-05-30

  Revised date: 2013-06-07

  Online published: 2013-06-21

Supported by

Project supported by the Foundation of Shanghai Municipal Commission of Economy and Informatization (No. 12CH-02)

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摘要

以最近开发的双膦-铑配合物[Rh((R,R)-QuinoxP*)(cod)]SbF6作为催化剂, 利用不对称催化氢化方法合成了一系列D-(R)-酪氨酸衍生物, 在S/C=10000条件下获得了99% ee的对映选择性. 并将所得的氢化产物成功应用于具有重要生理活性的化合物(R)-2-羟基-3-(3,4-二羟基苯基)丙酸钠的合成. 相比于已报道的方法, 该工艺路线产率更高而且不需要柱层析分离, 因而非常具有工业化应用前景.

关键词： 不对称催化氢化; D-(R)-酪氨酸; 铑; 双膦配体; (R)-2-羟基-3-(3,4-二羟基苯基)丙酸钠

本文引用格式

余坤矫 , 张振锋 , 霍小红 , 王兴广 , 刘德龙 , 张万斌 . D-(R)-酪氨酸的不对称催化氢化合成及其在药物合成中的应用[J]. 有机化学, 2013 , 33(9) : 1932 -1938 . DOI: 10.6023/cjoc201305051

Abstract

Using a recently developed catalyst[Rh((R,R)-QuinoxP*)(cod)]SbF6, several derivatives of D-(R)-tyrosine were prepared with up to 99% ee via catalytic asymmetric hydrogenation. The substrates chosen for asymmetric hydrogenation were readily synthesized from the inexpensive and accessible compound 4-hydroxybenzaldehyde. The product resulting from the asymmetric hydrogenation was practically applied to the preparation of an important bioactive compound sodium (R)-3-(3,4-dihydroxyphenyl)-2-hydroxypropanoate through a feasible process.

Key words： catalytic asymmetric hydrogenation; D-(R)-tyrosine; rhodium; biphosphine ligand; sodium (R)-3-(3,4-dihydr- oxyphenyl)-2-hydroxypropanoate

参考文献

[1] (a) Ujihara, Y.; Nakayama, K.; Sengoku, T.; Takahashi, M.; Yoda, H. Org. Lett. 2012, 14, 5142.
(b) Li, J.; Feng, Y. H.; Li, X. B.; Han, W.; Liu, H. Q.; Shao, G. G. Chin. Chem. Lett. 2012, 23, 647.
(c) Chen, G.; Huang, H.; Ye, J.; Wang, A.; Huang, H.; Zhang, H.; Huang, P. Chem. Asian J. 2012, 7, 504.
(d) Chen, Y.; Xu, Q.; Zhao, Z.; Wang, L.; Yu, P.; Chen, Q. J. Chin. Med. Mater. 2011, 34, 472 (in Chinese).
(陈永红, 续倩, 赵增超, 王磊, 于沛, 程潜, 中药材, 2011, 34, 472.)
(e) Descôteaux, C.; Leblanc, V.; Brasseur, K.; Gupta, A.; Asselin, Ė.; Bérubé, G. Bioorg. Med. Chem. Lett. 2010, 20, 7388.
(f) Ishigami, K.; Katsuta, R.; Shibata, C.; Hayakawa, Y.; Watanabe, H.; Kitahara, T. Tetrahedron 2009, 65, 3629.
(g) Katsuta, R.; Shibata, C.; Ishigami, K.; Watanabe, H.; Kitahara, T. Tetrahedron Lett. 2008, 49, 7042.
[2] (a) Chen, X.; Rao, J.; Wang, J.; Gooding, J. J.; Zou, G.; Zhang, Q. Chem. Commun. 2011, 47, 10317.
(b) Liu, Q.; Wu, K.; Tang, F.; Yao, L.; Yang, F.; Nie, Z.; Yao, S. Chem. Eur. J. 2009, 15, 9889.
(c) Tang, L.; Ga, H.; Kim, J.; Choi, S.; Nandhakumar, R.; Kim, K. M. Tetrahedron Lett. 2008, 49, 6914.
(d) Peng, Y.; He, Q.; Wang, J.; Gao, H.; Chai, S.; Tian, H. Chin. J. Org. Chem. 2006, 26, 69 (in Chinese).
(彭阳峰, 何佺, 王家荣, 高浩其, 蔡水洪, 田禾, 有机化学, 2006, 26, 69.)
[3] (a) Gong, X.; Su, E.; Wang, P.; Wei, D. Tetrahedron Lett. 2011, 52, 5398.
(b) Zhang, Z. Tetrahedron Lett. 2008, 49, 6468.
(c) Nozaki, H.; Takenaka, Y.; Kira, I.; Watanabe, K.; Yokozeki, K. J. Mol. Catal. B: Enzym. 2005, 32, 213.
(d) Patel, R. N.; Nanduri, V.; Brzozowski, D.; McNamee, C.; Banerjee, A. Adv. Synth. Catal. 2003, 345, 830.
(e) Alexandre, F.; Pantaleone, D. P.; Taylor, P. P.; Fotheringham, I. G.; Ager, D. J.; Turner, N. J. Tetrahedron Lett. 2002, 43, 707.
[4] (a) Bae, H.; Lee, S.; Hong, S.; Kwak, M.; Esaki, N.; Soda, K.; Sung, M. J. Mol. Catal. B: Enzym. 1999, 6, 241.
(b) Galkin, A.; Kulakova, L.; Yamamoto, H.; Tanizawa, K.; Tanaka, H.; Esaki, N.; Soda, K. J. Ferm. Bioeng. 1997, 83, 299.
(c) Kuang, H.; Davies, R. R.; Distefano, M. D. Bioorg. Med. Chem. Lett. 1997, 7, 2055.
(d) Galkin, A.; Kulakova, L.; Yoshimura, T.; Soda. K.; Esaki, N. Appl. Environ. Microbiol. 1997, 63, 4651
[5] (a) Etayo, P.; Vidal-Ferran, A. Chem. Soc. Rev. 2013, 42, 728.
(b) Tsuneo, I. In Hydrogenation, Ed.: Karamé, I., InTech, 2012, Chapter 1 (ISBN: 978-953-51-0785-9, DOI: 10.5772/48584. Available from: http://www.intechopen.com/books/hydrogenation/ asymmetric-hydrogenation).
(c) Wang, J.; Liu, D.; Liu, Y.; Zhang, W. Org. Biomol. Chem. 2013, 11, 3855.
(d) Liu, Y.; Zhang, W. Angew. Chem., Int. Ed. 2013, 55, 2203.
(e) Liu, Y.; Wang, Z.; Ding, K. Acta Chim. Sinica 2012, 70, 1464 (in Chinese).
(刘龑, 王正, 丁奎岭, 化学学报, 2012, 70, 1464.)
(f) Xie, J.; Zhou, Q. Acta Chim. Sinica 2012, 70, 1427 (in Chinese).
(谢建华, 周其林, 化学学报, 2012, 70, 1427.)
(g) Yao, D.; Tian, F.; Zhang, W. Chin. J. Org. Chem. 2011, 31, 505 (in Chinese).
(姚冬梅, 田丰涛, 张万斌, 有机化学, 2011, 31, 505.)
(h) Zhang, Z.; Xie, F.; Yang, B.; Yu, H.; Zhang, W. Chin. J. Org. Chem. 2011, 31, 429 (in Chinese).
(张振锋, 谢芳, 杨波, 余焓, 张万斌, 有机化学, 2011, 31, 429.)
(i) Tian, F.; Yao, D.; Liu, Y.; Xie, F.; Zhang, W. Adv. Synth. Catal. 2010, 352, 1841.
(j) Blaser, H.-U.; Federsel, H.-J. Asymmetric Catalysis on Industrial Scale, 2nd ed., Wiley-VCH, Weinheim, Germany, 2010.
(k) Li, Y.; Zheng, Y.; Tian, F.; Zhang, Y. J.; Zhang, W. Chin. J. Org. Chem. 2009, 29, 1487 (in Chinese).
(李亚玺, 郑玉林, 田丰涛, 张勇健, 张万斌, 有机化学, 2009, 29, 1487.)
(l) Dai, Y.; Yang, G.; Zhang, Y. J.; Wang, F.; Zhang, W. Chin. J. Org. Chem. 2008, 28, 1169 (in Chinese).
(戴轶俊, 杨国强, 张勇健, 王飞军, 张万斌, 有机化学, 2008, 28, 1169.)
(m) Ma, Y.; Zhang, Y. J.; Zhang, W. Chin. J. Org. Chem. 2007, 27, 289 (in Chinese).
(马元辉, 张勇健, 张万斌, 有机化学, 2007, 27, 289.)
(n) de Vries, J. G.; Elsevier, C. J. Handbook of Homogeneous Hydrogenation, Wiley-VCH, Weinheim, Germany, 2007.
[6] (a) Chen, Y.; Li, Y.; Lam, K.; Chan, A. S. C. Chin. J. Chem. 2003, 21, 66.
(b) Jia, X.; Li, X.; Xu, L.; Shi, Q.; Yao, X.; Chan, A. S. C. J. Org. Chem. 2003, 68, 4539.
(c) Guo, R.; Li, X.; Wu, J.; Kwok, W. H.; Chen, J.; Choi, M. C. K.; Chan, A. S. C. Tetrahedton Lett. 2002, 43, 6803.
(d) Guo, R.; Au-Yeung, T. T. L.; Wu, J.; Choi, M. C. K.; Chan, A. S. C. Tetrahedron: Asymmetry 2002, 13, 2519.
(e) Li, X.; Lou, R.; Yeung, C.; Chan, A. S. C.; Wong, W. K. Tetrahedron: Asymmetry 2000, 11, 2077.
(f) Chen, Y.; Li, X.; Tong, S.; Choi, M. C. K.; Chan, A. S. C. Tetrahedron Lett. 1999, 40, 957.
(g) Terfort, A. Synthesis 1992, 951.
(h) Takahashi, H.; Achiwa, K. Chem. Lett. 1989, 305.
(i) Johnson, C. R.; Imamoto, T. J. Org. Chem. 1987, 52, 2170.
(j) Saito, K.; Saijo, S.; Kotera, K.; Date, T. Chem. Pharm. Bull. 1985, 33, 1342.
(k) MacNeil, P. A.; Roberts, N. K.; Bosnich, B. J. Am. Chem. Soc. 1981, 103, 2273.
(l) Baker, G. L.; Fritschel, S. J.; Stille, J. R.; Stille, J. K. J. Org. Chem. 1981, 46, 2954.
(m) Fryzuk, M. D.; Bosnich, B. J. Am. Chem. Soc. 1977, 99, 6262.
(n) Achiwa, K. J. Am. Chem. Soc. 1976, 98, 8265.
[7] The ether derivatives such as 1e and 1f are widely studied in asymmetric hydrogenation but less suitable for industrial application for the relatively difficult demethylation process. For the recent representative literatures, see:
(a) Huang, K.; Zhang, X.; Emge, T. J.; Hou, G.; Cao, B.; Zhang, X. Chem. Commun. 2010, 8555.
(b) Fernádez-Pérez, H.; Donald, S. M. A.; Munslow, I. J.; Benet-Buchholz, J. B.; Maseras, F.; Vidal-Ferran, A. Chem. Eur. J. 2010, 16, 6495.
(c) Zhang, X.; Huang, K.; Hou, G.; Cao, B.; Zhang, X. Angew. Chem., Int. Ed. 2010, 49, 6421.
(d) Sun, X.; Li, W.; Zhou, L.; Zhang, X. Adv. Synth. Catal. 2010, 352, 1150.
(e) Tang, W.; Capacci, A. G.; Ma, S.; Rodriguez, S.; Qu, B.; Savoie, J.; Patel, N. D.; Wei, X.; Haddad, N.; Grinberg, N.; Yee, N. K.; Krishnamurthy, D.; Senanayake, C. H.; White, A. Org. Lett. 2010, 12, 1104.
(f) Tang, W.; Qu, B.; Capacci, A. G.; Rodriguez, S.; Wei, X.; Haddad, N.; Narayanan, B.; Ma, S.; Grinberg, N.; Yee, N. K.; Krishnamurthy, D.; Senanayake, C. H. Org. Lett. 2010, 12, 176.
(g) Wu, H.; Hamid, S. A.; Yu, J.; Spencer, J. B. J. Am. Chem. Soc. 2009, 131, 9604.
(h) Hattori, G.; Hori, T.; Miyake, Y.; Nishibayashi, Y. J. Am. Chem. Soc. 2007, 129, 12930.
(i) Giacomina, F.; Meetsma, A.; Panella, L.; Lefort, L.; de Vries, A. H. M.; de Vries, J. G. Angew. Chem., Int. Ed. 2007, 46, 1497.
[8] (a) Imamoto, T.; Tamura, K.; Zhang, Z.; Horiuchi, Y.; Sugiya, M.; Yoshida, K.; Yanagisawa, A.; Gridnev, I. D. J. Am. Chem. Soc. 2012, 134, 1754.
For similar catalyst with the anion of BF4-, see: (b) Imamoto, T.; Sugita, K.; Yoshida, K. J. Am. Chem. Soc. 2005, 127, 11934.
[9] (a) Tong, Y.; Guo, X.; Cheng, Y.; Wu, S. Chin. J. Med. Chem. 2007, 17, 92 (in Chinese).
(童元峰, 郭晓, 程永浩, 吴松, 中国药物化学杂志, 2007, 17, 92.)
(b) Deng, X.; Chen, X.; Jiang, F.; Yao, X. Chin. J. Pharm. 2005, 36, 523 (in Chinese).
(邓喜玲, 陈学敏, 江发寿, 姚新成, 中国医药工业杂志, 2005, 36, 523.)
(c) Wong, H. N. C.; Xu, Z. L.; Chang, H. M.; Lee, C. M. Synthesis 1992, 793.
(d) Xue, F.; Dai, H.; Ding, L. Acta Acad. Med. Prim. Shanghai 1983, 10, 133 (in Chinese).
(薛芬, 戴华娟, 丁丽蓉, 上海第一医学院学报, 1983, 10, 133.)
[10] Zhang, D.; Wu, W.; Liu, X.; Pan, D.; Yang, C.; Zhang, B. Acta Acad. Med. Prim. Shanghai 1980, 7, 384 (in Chinese).
(张德成, 吴伟良, 刘星堦, 潘德济, 上海第一医学院学报, 1980, 7, 384.)
[11] For reports on the synthesis of enantiopure danshensu catalyzed by enzyme, see:
(a) Findrik, Z.; Poljanac, M.; Vasić-Rački, Đ. Chem. Biochem. Eng. Q. 2005, 19, 351.
(b) Pabsch, K.; Rao, N. N.; Wandrey, C.; Petersen, M.; Alfermann, A. W. Recl. Trav. Chim. Pays-Bas 1991, 110, 199.
For reports on the synthesis of enantiopure derivatives of danshensu catalyzed by osmium, see. (c) Tian, H.; Zhou, X.; Chen, M.; Wu, J.; Zhen, X.; Jiang, R. Chin. J. Med. Chem. 2012, 22, 113 (in Chinese).
(田海林, 周晓伟, 陈明, 吴剑峰, 郑晓晖, 姜茹, 中国药物化学杂志, 2012, 22, 113.)
(d) Chen, M.; Chen, H.; Wang, Y.; Wang, H.; Nan, Y.; Zheng, X.; Jiang, R. Tetrahedron: Asymmetry 2011, 22, 4.
[12] (a) Bogucki, D. E.; Charlton, J. L. Can. J. Chem. 1997, 75, 1783.
(b) Wünsch, B.; Zott, M. Liebigs Ann. Chem. 1992, 39.
[13] During our research, Yu's group developed a similar method for the synthesis of sodium danshensu with R configuration from D-(R)-tyrosine[1d]. However, the yield is low and the operation is complicated.
[14] Stafforst, T.; Diederichsen, U. Eur. J. Org. Chem. 2007, 899.
[15] Losse, G.; Hebel, H.; Kästner, C. J. Prakt. Chem. 1959, 8, 339.
[16] (a) Ranganathan, S.; Tamilarasu, N. Tetrahedron Lett. 1994, 35, 447; (b) Boger, D. L.; Yohannes, D. J. Org. Chem. 1987, 52, 5283; (c) Bretschneider, H.; Hohenlohe-Oehrinģen, K.; Kaiser, A.; Wölcke, U. Helv. Chim. Acta 1973, 56, 2857.
[17] Young, J. US 2006/0083798, 2006[Chem. Abstr. 2006, 144, 37645].
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