生物碱Peduncularine的合成策略和方法
收稿日期: 2018-10-09
修回日期: 2018-11-22
网络出版日期: 2018-12-05
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
Received date: 2018-10-09
Revised date: 2018-11-22
Online published: 2018-12-05
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).
（-）-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
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 . DOI: 10.6023/cjoc201810008
(-)-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.
[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.
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