生物碱Peduncularine的合成策略和方法

doi:10.6023/cjoc201810008

有机化学 ›› 2019, Vol. 39 ›› Issue (1): 47-58.DOI: 10.6023/cjoc201810008 上一篇下一篇

所属专题：庆祝陈庆云院士九十华诞

综述与进展

生物碱Peduncularine的合成策略和方法

章玉平^a, 田学超^a, 张岩^b, 洪然^b, 黄莎华^a,b

a 上海应用技术大学化学与环境工程学院上海 201418;
b 中国科学院上海有机化学研究所中国科学院天然产物有机合成化学重点实验室分子合成卓越创新中心上海 200032

收稿日期:2018-10-09 修回日期:2018-11-22 发布日期:2018-12-05
通讯作者: 洪然, 黄莎华 E-mail:rhong@sioc.ac.cn;shahua@sit.edu.cn
基金资助:
国家自然科学基金（No.21402121）和上海应用技术大学协同创新计划（No.XTCX2015-16）项目资助.

Methods and Strategies for the Synthesis of Peduncularine

Zhang Yuping^a, Tian Xuechao^a, Zhang Yan^b, Hong Ran^b, Huang Shahua^a,b

a School of Chemical and Environmental Engineering, Shanghai Institute of Technology, Shanghai 201418;
b CAS Key Laboratory of Synthetic Chemistry of Natural Substances, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032

Received:2018-10-09 Revised:2018-11-22 Published:2018-12-05
Contact: 10.6023/cjoc201810008 E-mail:rhong@sioc.ac.cn;shahua@sit.edu.cn
Supported by:
Project supported by the National Natural Science Foundation of China (No. 21402121) and the Collaborative Innovation Program of Shanghai Institute of Technology (No. XTCX2015-16).

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摘要/Abstract

（-）-Peduncularine是从塔斯玛尼亚灌木Aristotelia peduncularis中分离得到的生物碱，含吲哚结构单元且含有高张力的6-氮杂双环[3.2.1]辛烷核心骨架.由于其独特的结构，受到合成化学家的极大关注.目前，已有多个课题组对其展开了全合成研究.本文将介绍近年来不同研究小组所发展peduncularine的合成策略，对于药物合成研究中类似特殊环系的构建提供借鉴.

关键词: 6-氮杂双环[3.2.1]辛烷, 成环反应, 吲哚生物碱, peduncularine, 全合成

(-)-Peduncularine is the principal alkaloid isolated from Tasmanian shrub Aristotelia peduncularis. Due to its unusual 6-azabicyclo[3.2.1]octane core, the indole alkaloid was received numerous attention from the synthetic community and several innovative synthetic strategies have been developed. In this minireview, the synthetic efforts of peduncularine are summarized as inspiration for future development of medicinally interesting derivatives.

Key words: 6-azabicyclo[3.2.1]octane, cyclization, indole alkaloids, peduncularine, total synthesis

引用此文

章玉平, 田学超, 张岩, 洪然, 黄莎华. 生物碱Peduncularine的合成策略和方法[J]. 有机化学, 2019, 39(1): 47-58.

Zhang Yuping, Tian Xuechao, Zhang Yan, Hong Ran, Huang Shahua. Methods and Strategies for the Synthesis of Peduncularine[J]. Chin. J. Org. Chem., 2019, 39(1): 47-58.

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参考文献

[1] (a) Butler, M. S. J. Nat. Prod. 2004, 67, 2141.
(b) Li, J. W.-H.; Vederas, J. C. Science 2009, 325, 161.
(c) Newman, D. J.; Cragg, G. M. J. Nat. Prod. 2016, 79, 629.
(d) DeCorte, B. L. J. Med. Chem. 2016, 59, 9295.
[2] Lawson, A. D. G.; MacCoss, M.; Heer, J. P. J. Med. Chem. 2018, 61, 4283.
[3] Over, B.; Wetzel, S.; Grütter, C.; Nakai, Y.; Renner, S.; Rauh, D.; Waldmann, H. Nat. Chem. 2013, 5, 21.
[4] Bick, I. R. C.; Bremner, J. B.; Preston, N. W.; Calder, I. C. J. Chem. Soc., Chem. Commun. 1971, 1155.
[5] Ros, H.-P.; Kyburz, R.; Preston, N. W.; Gallagher, R. T.; Bick, I. R. C.; Hesse, M. Helν. Chim. Acta 1979, 62, 481.
[6] Bick, I. R. C.; Hai, M. A.; Preston, N. W. Tetrahedron 1985, 41, 3127.
[7] Klaver, W. J.; Hiemstra, H.; Speckamp, W. N. J. Am. Chem. Soc. 1989, 111, 2588.
[8] Dragar, C.; Bick, I. R. C. Phytochemistry 1992, 31, 3601.
[9] (a) Singh, S. Chem. Rev. 2000, 100, 925.
(b) Pollini, G. P.; Benetti, S.; De Risi, C.; Zanirato, V. Chem. Rev. 2006, 106, 2434.
[10] (a) Carroll, F. I.; Abraham, P.; Parham, K.; Griffith, R. C.; Ahmad, A.; Richard, M. M.; Padilla, F. N.; Witkin, J. M.; Chiang, P. K. J. Med. Chem. 1987, 30, 805.
(b) Carroll, F. I.; Abraham, P.; Mascarella, S. W.; Singh, P.; Moreland, C. G.; Sankar, S. S.; Kwon, Y. W.; Triggle, D. J. J. Med. Chem. 1991, 34, 1436.
[11] Quirante, J.; Vila, X.; Bonjoch, J.; Kozikowski, A. P.; Johnson, K. M. Bioorg. Med. Chem. 2004, 12, 1383.
[12] Holmes, A. B.; Kee, A.; Ladduwahetty, T.; Smith, D. F. J. Chem. Soc., Chem. Commun. 1990, 1412.
[13] Chamberlin, A. R.; Chung, J. Y. L. J. Am. Chem. Soc. 1983, 105, 3653.
[14] (a) Hiemstra, H.; Speckamp, W. N. Tetrahedron Lett. 1983, 24, 1407.
(b) Hiemstra, H.; Klaver, W. J.; Speckamp, W. N. J. Org. Chem. 1984, 49, 1149.
[15] Thomsen, I.; Clausen, K.; Scheibye, S.; Lawesson, S.-O. Org. Synth. 1984, 62, 158.
[16] Robinson, B. Chem. Rev. 1969, 69, 227.
[17] Rigby, J. H.; Meyer, J. H. Synlett 1999, 860.
[18] Rigby, J. H.; Ateeq, H. S.; Charles, N. R.; Henshilwood, J. A.; Short, K. M. Sugathapala, P. M. Tetrahedron 1993, 49, 5495.
[19] McKillop, A.; Hunt, J. D.; Kienzle, F.; Bigham, E.; Taylor, E. C. J. Am. Chem. Soc. 1973, 95, 3635.
[20] Lin, X.; Stien, D.; Weinreb, S. M. Tetrahedron Lett. 2000, 41, 2333.
[21] (a) Hudson, R. F.; Record, K. A. F. J. Chem. Soc., Perkin. 21978, 822.
(b) Lin, X.; Stien, D.; Weinreb, S. M. Org. Lett. 1999, 1, 637.
[22] (a) Washburn, D. G.; Heidebrecht, R. W., Jr.; Martin, S. F. Org. Lett. 2003, 5, 3523.
(b) Martin, S. F. Pure Appl. Chem. 2005, 77, 1207.
[23] (a) Brown, D. S.; Hansson, T.; Ley, S. V. Synlett 1990, 48.
(b) Brown, D. S.; Charreu, P.; Hansson, T.; Ley, S. V. Tetrahedron 1991, 47, 1311.
[24] Roberson, C. W.; Woerpel, K. A. Org. Lett. 2000, 2, 621.
[25] Durst, T.; O'Sullivan, M. J. J. Org. Chem. 1970, 35, 2043.
[26] Roberson, C. W.; Woerpel, K. A. J. Org. Chem. 1999, 64, 1434.
[27] Dubé, D.; Scholte, A. A. Tetrahedron Lett. 1999, 40, 2295.
[28] Groaning, M. D.; Brengel, G. P.; Meyers, A. I. J. Org. Chem. 1998, 63, 5517.
[29] Tamao, K.; Ishida, N.; Tanaka, T.; Kumada, M. Organometallics 1983, 2, 1694.
[30] Roberson, C. W.; Woerpel, K. A. J. Am. Chem. Soc. 2002, 124, 11342.
[31] Shute, R. E.; Rich, D. H. Synthesis 1987, 346.
[32] (a) Hosomi, A.; Sakurai, H. Tetrahedron Lett. 1976, 17, 1295.
(b) Speckamp, W. N.; Moolenaar, M. J. Tetrahedron 2000, 56, 3817.
[33] Roush, W. R.; Gillis, H. R. J. Org. Chem. 1980, 45, 4283.
[34] Abdel-Magid, A. F.; Carson, K. G.; Harris, B. D.; Maryanoff, C. A.; Shah, R. D. J. Org. Chem. 1996, 61, 3849.
[35] Smitrovich, J. H.; Woerpel, K. A. J. Org. Chem. 1996, 61, 6044.
[36] Parikh, J. R.; Doering, W. E. J. Am. Chem. Soc. 1967, 89, 5505.
[37] Cannizzo, L. F.; Grubbs, R. H. J. Org. Chem. 1985, 50, 2386.
[38] Hodgson, D. M.; Shelton, R. E.; Moss, T. A.; Dekhane, M. Org. Lett. 2010, 12, 2834.
[39] Mann, J.; de Almeida Barbosa L.-C. J. Chem. Soc., Perkin Trans. 1 1992, 787.
[40] Davies, H. M. L.; Cao, G. Tetrahedron Lett. 1998, 39, 5943.
[41] Swallen, L. C.; Boord, C. E. J. Am. Chem. Soc. 1930, 52, 651.
[42] Kitamura, M.; Ihara, R.; Uera, Y.; Narasaka, K. Bull. Chem. Soc. Jpn. 2006, 79, 1552.
[43] (a) Uchiyama, K.; Ono, A.; Hayashi, Y.; Narasaka, K. Bull. Chem. Soc. Jpn. 1998, 71, 2945.
(b) Uchiyama, K.; Hayashi, Y.; Narasaka, K. Chem. Lett. 1998, 1261.
[44] Kotsuki, H.; Asao, K.; Ohnishi, H. Bull. Chem. Soc. Jpn. 1984, 57, 3339.
[45] Lenz, G. R.; Woo, C-M.; Hawkins, B. L. J. Org. Chem. 1982, 47, 3049.
[46] (a) Hudrlik, P. F.; Peterson, D. J. Am. Chem. Soc. 1975, 97, 1464.
(b) Johnson, C. R.; Tait, B. D. J. Org. Chem. 1987, 52, 281.
[47] Ragains, J. R.; Winkler, J. D. Org. Lett. 2006, 8, 4437.
[48] (a) Winkler, J. D.; Muller, C. L.; Scott, R. D. J. Am. Chem. Soc. 1988, 110, 4831.
(b) Kwak, Y.-S.; Winkler, J. D. J. Am. Chem. Soc. 2001, 123, 7429.
[49] Comins, D. L; Dehghani. A. Tetrahedron Lett. 1992, 33, 6299.
[50] Jigqjinni, V. B.; Wightman, R. H. Tetrahedron Lett. 1982, 23, 117.
[51] (a) Kyburz, R.; Schöpp, E.; Hesse, M.; Bick, I. R. C. Helv. Chim. Acta 1979, 62, 2539.
(b) Bick, I. R. C.; Hai, M. A.; Preston, N. W. Tetrahedron Lett. 1988, 29, 3355.
(c) Anderson, B. F.; Robertson, G. B.; Avey, P.; Donovan, W. F.; Bick, I. R. C.; Bremner, J. B.; Finney, A. J.T.; Preston, N. W.; Gallagher, R. T.; Russell, G. B. J. Chem. Soc., Chem. Commun. 1975, 511.
(d) Bittner, M.; Silva, M.; Gopalakrishna, E. M.; Watson, W. H.; Zabel, V.; Matlin, S. A.; Sammes, P. G. J. Chem. Soc., Chem. Commun. 1978, 79.
[52] (a) Bick, I. R. C.; Hai, M. A.; Preston, N. W. Heterocycles 1979, 12, 1563.
(b) Saxton, J. E. Nat. Prod. Rep. 1994, 11, 493.
(c) An elegant review on the biomimetic synthesis study of aristotelia alkaloids, see:Borschberg, H.-J. In The Alkaloids: Chemistry and Pharmacology, Vol. 48, Ed.:Cordell, G. A., Elsevier, Academic Press, 1996, Chapter 3, pp. 191~248.
[53] (a) Lovering, F.; Bikker, J.; Humblet, C. J. Med. Chem. 2009, 52, 6752.
(b) Szychowski, J.; Truchon, J.-F.; Bennani, Y. L. J. Med. Chem. 2014, 57, 9292.
(c) Stockdale, T. P.; Williams. C. M. Chem. Soc. Rev. 2015, 44, 7737.
[54] (a) Tamura, O.; Yanagimachi, T.; Kobayashi, T.; Ishibashi, H. Org. Lett. 2001, 3, 2427.
(b) Zhai, H.-B.; Luo, S.-J.; Ye, C.-F.; Ma, Y.-X. J. Org. Chem. 2003, 68, 8268.
(c) Yeung, Y. Y.; Hong, S.-W.; Corey, E. J. J. Am. Chem. Soc. 2006, 128, 6310.
(d) Grainger, R. S.; Welsh, E. J. Angew. Chem., Int. Ed. 2007, 46, 5477.
(e) Campbell, C. L.; Hassler, C.; Ko, S. S.; Voss, M. E.; Guaciaro, M. A.; Carter, P. H.; Cherney, R. J. J. Org. Chem. 2009, 74, 6368.
[55] Kanchupalli, V.; Katukojvala, S. Angew. Chem., Int. Ed. 2018, 57, 5433.
[56] Zhan, Y.-Z.; Liu, T.; Wang, Z.-W. Chem. Eur. J. 2017, 23, 17862.
[57] Mackiewicz, P.; Furstoss, R.; Waegell, B. J. Org. Chem. 1978, 43, 3746.
[58] Liu, T.; Mei, T.-S.; Yu, J.-Q. J. Am. Chem. Soc. 2015, 137, 5871.
[59] Holmes, A. B.; Raithby, P. R.; Thompson, J.; Baxter, A. J. G.; Dixon, J. J. Chem. Soc., Chem. Commun. 1983, 1490.
[60] (a) Callis, D. J.; Thomas, N. F.; Pearson, D. P. J.; Potter, B. V. L. J. Org. Chem. 1996, 61, 4634.
(b) Kumar, P.; Li, P.-H.; Korboukh, I.; Wang, T. L.; Yennawar, H.; Weinreb,S. M. J. Org. Chem. 2011, 76, 2094.
[61] (a) Xie, C.; Luo, J.; Zhang, Y.; Huang, S.-H.; Zhu, L.; Hong, R. Org. Lett. 2018, 20, 2386.
(b) Luo, J.; Xie, C.; Zhang, Y.; Huang, S.-H.; Zhu, L.; Hong, R. Tetrahedron 2018, 74, 5791.
[62] Quirante, J.; Vila, X.; Escolano, C.; Bonjoch, J. J. Org. Chem. 2002, 67, 2323.
[63] Grainger, R. S.; Betou, M.; Male, L.; Pitak, M. B.; Coles, S. J. Org. Lett. 2012, 14, 2234.
[64] Walker, P. D.; Campbell, C. D.; Suleman, A.; Carr, G.; Anderson, E. A. Angew. Chem., Int. Ed. 2013, 52, 9139.
[65] Yeh, M.-C. P.; Chang, Y.-M.; Lin, H.-H. Adv. Synth. Catal. 2017, 359, 2196.

生物碱Peduncularine的合成策略和方法

Methods and Strategies for the Synthesis of Peduncularine

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