Asymmetric Total Synthesis of (－)-Cephalotaxine

doi:10.6023/cjoc201705025

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Chen Yang, Li Wei-Dong Z. Asymmetric Total Synthesis of (－)-Cephalotaxine[J]. Chin. J. Org. Chem., 2017, 37(8): 1885-1902.

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[1] Wall, M. E.; Eddy, C. R.; Willaman, J. J.; Correll, D. S.; Schubert, B. G.; Gentry, H. S. J. Am. Pharm. Assoc., Sci. Ed. 1954, 43, 503.
[2] Paudler, W. W.; Kerley, G. I.; McKay, J. J. Org. Chem. 1963, 28, 2194.
[3] Abraham, D. J.; Rosenstein, R. D.; McGandy, E. L. Tetrahedron Lett. 1969, 10, 4085.
[4] Arora, S. K.; Bates, R. B.; Grady, R. A.; Powell, R. G. J. Org. Chem. 1974, 39, 1269.
[5] Powell, R. G.; Weisleder, D.; Smith, C. R. Jr. J. Pharm. Sci. 1972, 61, 1227.
[6] For cephalotaxus esters as anticancer and antileukemic agents from the 1970s in China, see:(a) Cephalotaxus Research Coordinating Group Chin. Med. J. (Engl.) 1976, 2, 263-272.
(b) Leukemia Research Group of the Chinese Liberation Army 187th Hospital Chin. Med. J. 1978, 58, 163(in Chinese). (中国人民解放军第一八七医院白血病研究小组, 中华医学杂志, 1978, 58, 163.)
(c) Pharmacopoeia Committee of Ministry of Health Chinese Pharmacopoeia, 1990 Edition Ⅱ, People's Health Pub House, Beijing, 1990, pp. 588~590(in Chinese). (中华人民共和国卫生部药典委员会, 中华人民共和国药典1990年版二部, 人民卫生出版社, 北京, 1990, pp. 588~590.)
[7] For Homoharringtonine/Omacetaxine Mepesuccinate (FDA), see:(a) Kantarjian, H. M.; O'Brien, S.; Cortes, J. Clin. Lymphoma Myeloma Leuk. 2013, 13, 530.
(b) Heiblig, M.; Sobh, M.; Nicolini, F. E. Leuk Res. 2014, 38, 1145.
[8] For diastereoselective synthesis of cephalotaxus esters via asymmetric Mukaiyama Aldol reaction, see:Ma, G. -Z.; Li, P. -F.; Liu, L.; Li, W. -D. Z.; Chen, L. Org. Lett. 2017, 19, 2250.
[9] For semisynthesis of homoharringtonine from cephalotaxine, see:(a) Wang, Y.-K.; Li, Y.-L.; Pan, S.-F.; Li S.-B.; Huang, W.-K. Sci. Bull. 1980, 25, 576(in Chinese). (王永铿, 李裕林, 潘鑫复, 李绍白, 黄文魁, 科学通报, 1980, 25, 576.)
(b) Wang, Y.-K.; Li, Y.-L.; Pan, S.-F.; Li S.-B.; Huang, W.-K. J. Lanzhou Univ., Nat. Sci. 1980, 71(in Chinese). (王永铿, 李裕林, 潘鑫复, 李绍白, 黄文魁, 兰州大学学报(自然科学版), 1980, 71.)
(c) Zhao, Z.-Z.; Xi, Y.-G.; Zhao, H.-F.; Hou, J.-Y.; Zhang J.-Y.; Wang, Z.-H. Acta Pharm. Sin. 1980, 15, 46(in Chinese). (赵知中, 席与珪, 赵翰飞, 侯建英, 张建友, 王子厚, 药学学报, 1980, 15, 46.)
(d) Hiranuma, S.; Hudlicky, T. Tetrahedron Lett. 1982, 23, 3431.
(e) Hiranuma, S.; Shibata, M.; Hudlicky, T. J. Org. Chem. 1983, 48,5321.
(f) Cheng, J. -C.; Zhang, J. -H.; Zhang, Q. -B.; Yang J.; Huang, L. Acta Pharm. Sin. 1984, 19, 178(in Chinese). (程家宠, 张建华, 张千兵, 杨晶, 黄量, 药学学报, 1984, 19, 178.)
(g) Wang, Y.-K.; Li, Y.-L.; Pan, S.-F.; Li S.-B.; Huang, W.-K. Acta Chim. Sinica 1985, 43, 161(in Chinese). (王永铿, 李裕林, 潘鑫复, 李绍白, 黄文魁, 化学学报, 1985, 43, 161.)
(h) Robin, J. P.; Dhal, R.; Dujardin, G.; Girodier, L.; Mevellec, L.; Poutot, S. Tetrahedron Lett. 1999, 40, 2931.
[10] For the optical instability of cephalotaxine, see:Huang, W.-K.; Li, Y.-L.; Pan, S.-F. Sci. China, Ser. A 1979, 12, 1171(in Chinese). (黄文魁, 李裕林, 潘鑫复, 中国科学, 1979, 12, 1171.)
[11] For Liang's racemization mechanism hypothesis of cephalotaxine, see:(a) Liang, X.-T. In Chemistry of Natural Products-The Proceedings of Sino-American Symposium on Chemistry of Natural Products, Ed.:Wang, Y., Science Press, Beijing, 1982, pp. 19~28.
(b) Liang, X.-T. Chin. J. Org. Chem. 1981, 1, 243(in Chinese). (梁晓天, 有机化学, 1981, 1, 243.)
[12] Isono, N.; Mori, M. J. Org. Chem. 1995, 60, 115.
[13] Abdelkafi, H.; Nay, B. Nat. Prod. Rep. 2012, 29, 845.
[14] For reviews of (-)-cephalotaxine, see:(a) Niu, D.; Yan, W.; Sharif, E.; Rajaratnam, M.; O'Doherty, G. A. Chemtracts:Org. Chem. 2009, 22, 89.
(b) Zeng, B.-B.; Ren, J.-Y. Medicinal Natural Products-Total Synthetic Approaches, East China University of Science and Technology Press, Shanghai, 2016, pp. 88~118(in Chinese). (曾步兵, 任江萌, 药用天然产物全合成:合成路线精选, 华东理工大学出版社, 上海, 2016, pp. 88~118.)
[15] Taniguchi, T.; Ishibashi, H. Org. Lett. 2008, 10, 4129.
[16] Esmieu, W. R.; Worden, S. M.; Catterick, D.; Wilson, C.; Hayes, C. J. Org. Lett. 2008, 10, 3045.
[17] Ikeda, M.; El Bialy, S. A. A.; Hirose, K.; Kotake, M.; Sato, T.; Bayomi, S. M. M.; Shehata, I. A.; Abdelal, A. M.; Gad, L. M.; Yakura, T. Chem. Pharm. Bull. 1999, 47, 983.
[18] Hameed, A.; Blake, A. J.; Hayes, C. J. J. Org. Chem. 2008, 73, 8045.
[19] (a) Planas, L.; Perard-Viret, J.; Royer, J. J. Org. Chem. 2004, 69, 3087.
(b) Baussanne, I.; Dudot, B.; Pérard-Viret, J.; Planas, L.; Royer, J. Arkivoc 2006, 7, 57.
(c) Berhal, F.; Perard-Viret, J.; Royer, J. Tetrahedron:Asymmetry 2010, 21, 325.
[20] Eckelbarger, J. D.; Wilmot, J. T.; Gin, D. Y. J. Am. Chem. Soc. 2006, 128, 10370.
[21] Liu, Q.; Ferreira, E. M.; Stoltz, B. M. J. Org. Chem. 2007, 72, 7352.
[22] Gonçalves-Martin, M. G.; Zigmantas, S.; Renaud, P. Helv. Chim. Acta 2012, 95, 2502.
[23] Jiang, B. In The 6th Lingnan Organic Chemistry Forum, Shenzhen, 2016, p. 10(in Chinese). (姜标, 第六届岭南有机化学论坛, 深圳, 2016, p. 10.)
[24] Seebach, D.; Boes, M.; Naef, R.; Schweizer, W. B. J. Am. Chem. Soc. 1983, 105, 5390.
[25] Ikeda, M.; Okano, M.; Kosaka, K.; Kido, M.; Ishibashi, H. Chem. Pharm. Bull. 1993, 41, 276.
[26] Kuehne, M. E.; Bornmann, W. G.; Parsons, W. H.; Spitzer, T. D.; Blount, J. F.; Zubieta, J. J. Org. Chem. 1988, 53, 3439.
[27] Marguerit, M.; Little, G.; Wang, Y.; He, L.; Allwein, S.; Reif, J.; Rossi, J.; Roemmele, R.; Bakale, R. Eur. J. Org. Chem. 2015, 2015, 8003.
[28] Tietze, L. F.; Schirok, H. J. Am. Chem. Soc. 1999, 121, 10264.
[29] Zhang, Q.-W.; Xiang, K.; Tu, Y.-Q.; Zhang, S.-Y.; Zhang, X.-M.; Zhao, Y.-M.; Zhang, T.-C.; Chem. Asian J. 2012, 7, 894.
[30] Zhong, S.-B.; Liu, W.-Q.; Ling, Y.-Z.; Li, R.-L.; Tu, G.-Z.; Ma, L.-B.; Feng, S.-L. Chin. J. Med. Chem. 1994, 4, 84(in Chinese). (钟三保, 刘维勤, 凌仰之, 李仁利, 涂光忠, 马立斌, 冯少良, 中国药物化学杂志, 1994, 4, 84.)
[31] Robin, J.-P.; Blanchard, J.; Radosevic, N.; Roisnel, T.; Bataille, T. WO 2015162217, 2015[Chem. Abstr. 2015, 163, 656468].
[32] Nagasaka, T.; Sato, H.; Saeki, S. Tetrahedron:Asymmetry 1997, 8, 191.
[33] El Bialy, S. A. A.; Ismail, M. A.; Gad, L. M.; Abdelal, A. M. M. Med. Chem. Res. 2002, 11, 293.
[34] Zhao, Z.; Mariano, P. S. Tetrahedron 2006, 62, 7266.
[35] Auerbach, J.; Weinreb, S. M. J. Am. Chem. Soc. 1972, 94, 7172.
[36] Yasuda, S.; Yamada, T.; Hanaoka, M. Tetrahedron Lett. 1986, 27, 2023.
[37] Suga, S.; Watanabe, M.; Yoshida, J.-I. J. Am. Chem. Soc. 2002, 124, 14824.
[38] Li, W.-D. Z.; Wang, Y.-Q. Org. Lett. 2003, 5, 2931.
[39] (a) Li, W.-D. Z.; Ma, B.-C. J. Org. Chem. 2005, 70, 3277.
(b) Ma, B.-C.; Wang, Y.-Q.; Li, W.-D. Z. J. Org. Chem. 2005, 70, 4528.
(c) Li, W.-D. Z.; Yang, H. Tetrahedron 2005, 61, 5037.
(d) Yang, H.; Wang, Y-Q; Li, W.-D. Z. Chin. Chem. Lett. 2005, 16.
(e) Li, W.-D. Z.;Wang, X.-W. Org. Lett. 2007, 9, 1211.
[40] Zhao, Y.-M.; Gu, P.; Zhang, H.-J.; Zhang, Q.-W.; Fan, C.-A.; Tu, Y.-Q.; Zhang, F.-M. J. Org. Chem. 2009, 74, 3211.
[41] (a) Xing, P.; Huang, Z.-G.; Jin, Y.; Jiang, B. Synthesis 2013, 45, 596.
(b) Xu, Z.-L.; Xing, P.; Jiang, B. Org. Lett. 2017, 19, 1028.
[42] Xiao, K.-J.; Luo, J.-M.; Xia, X.-E.; Wang, Y.; Huang, P.-Q. Chem. Eur. J. 2013, 19, 13075.
[43] (a) Huang, S.-H.; Tian, X.; Mi, X.; Wang, Y.; Hong, R. Tetrahedron Lett. 2015, 56, 6656.
(b) Liu, H.; Yu, J.; Li, X.; Yan, R.; Xiao, J.-C.; Hong, R. Org. Lett. 2015, 17, 4444.
(c) Hong, R.; Wang, Y.; Ouyang, J.; Mi, X. Synlett 2017, 762.
[44] Zhang, Z.-W.; Zhang, X.-F.; Feng, J.; Yang, Y.-H.; Wang, C.-C.; Feng, J.-C.; Liu, S. J. Org. Chem. 2013, 78, 786.
[45] Sun, M.-R.; Lu, H.-T.; Wang, Y.-Z.; Yang, H.; Liu, H.-M. J. Org. Chem. 2009, 74, 2213.
[46] Ma, X.-Y.; An, X.-T.; Zhao, X.-H.; Du, J.-Y.; Deng, Y.-H.; Zhang, X.-Z.; Fan, C.-A. Org. Lett. 2017, 19, 2965.
[47] Li, S.-H. Ph.D. Dissertation, Naikai University, Tianjin, 2012(in Chinese). (李盛华, 博士论文, 南开大学, 天津, 2012.)
[48] Yong, S.-L. Ph.D. Dissertation, Naikai University, Tianjin, 2011(in Chinese). (雍胜利, 博士论文, 南开大学, 天津, 2011.)
[49] Zhuang, C.-H. Ph.D. Dissertation, Naikai University, Tianjin, 2010(in Chinese). (庄程翰, 博士论文, 南开大学, 天津, 2010.)
[50] Li, W.-D. Z.; Duo, W.-G.; Zhuang, C.-H. Org. Lett. 2011, 13, 3538.

天然三尖杉碱((－)-Cephalotaxine)的不对称全合成研究