白藜芦醇低聚物的化学选择性合成
收稿日期: 2013-08-19
修回日期: 2013-09-27
网络出版日期: 2013-09-30
基金资助
国家自然科学基金(No. 21062010)、兰州交通大学青蓝人才工程基金(No. QL-08-06A)资助项目.
Chemoselectively Synthesis of Resveratrol Oligomers
Received date: 2013-08-19
Revised date: 2013-09-27
Online published: 2013-09-30
Supported by
Project supported by the National Natural Science Foundation of China (No. 21062010), the "Qing Lan" Talent Engineering Funds of Lanzhou Jiaotong University (No. QL-08-06A).
李文玲, 吕腾, 杨玉华, 杨亚东 . 白藜芦醇低聚物的化学选择性合成[J]. 有机化学, 2013 , 33(12) : 2443 -2459 . DOI: 10.6023/cjoc201308023
Resveratrol oligomers are a class of plant polyphenols which are formed in nature by oxidative oligomerization of resveratrol catalyzed by enzymes and have received considerable attention of synthetic chemists on account of their structural complexity and diverse biological activities. The biomimetic synthetic strategy based on the oxidative coupling reaction has been extensively studied over the past thirty years, but the lacks of regio-or stereo-selectivity impose restrictions on its universal application. Recently, The synthetic efforts on the diverse skeletons of these oligomers through novel and effective cascade reactions has been a hot research topic and have achieved dramatic success. And they were mostly focused on the synthesis of racemates and the asymmetric synthesis research on these oligomers has just started. In this paper, the progress in the chemical syntheses of resveratrol oligomers in recent seven years is reviewed in detail and the future synthetic trend of oligostilbenes is also prospected.
Key words： resveratrol; oligomerization; chemoselectivity; total synthesis
[1] Shen, T.; Wang, X.-N.; Lou, H.-X. Nat. Prod. Rep. 2009, 26, 916.
[2] Sotheeswaran, S.; Pasupathy, V. Phytochemistry 1993, 32, 1083.
[3] Lin, M.; Yao, C. S. Stud. Nat. Prod. Chem. 2006, 33, 601.
[4] Langcake, P.; Pryce, R. J. Phytochemistry 1977, 16, 1193.
[5] Xiao, K.; Zhang, H. J.; Xuan, L. J.; Zhang, J.; Xu, Y. M.; Bai, D. L. Nat. Prod. Chem. 2008, 34, 453.
[6] Li, W. L.; Zang, P.; Li, H. F.; Yang, S. X. Prog. Chem. 2012, 24, 545 (in Chinese). (李文玲, 臧鹏, 李洪福, 杨世霞, 化学进展, 2012, 24, 545.)
[7] Quideau, S.; Deffieux, D.; Casassus, D.; Pouysegu, L. Angew. Chem., Int. Ed. 2011, 50, 586.
[8] Snyder, S. A.; Elsohly, A. M.; Kontes, F. Nat. Prod. Rep. 2011, 28, 897.
[9] Synder, S. A. Rec. Adv. Polyphenol. Res. 2012, 3, 311.
[10] Velu, S. S.; Thomas, N. F.; Weber, J. F. Curr. Org. Chem. 2012, 16, 605.
[11] Snyder, S. A.; Zografos, A. L.; Lin, Y.-Q. Angew. Chem., Int. Ed. 2007, 46, 8186..
[12] Snyder, S. A.; Breazzano, S. P.; Ross, A. G.; Lin, Y.-Q.; Zografos, A. L. J. Am. Chem. Soc. 2009, 131, 1753.
[13] Snyder, S. A.; Wright, N. E.; Pflueger, J. J.; Breazzano, S. P. Angew. Chem., Int. Ed. 2011, 50, 8629.
[14] Snyder, S. A.; Thomas, S. B.; Mayer, A. C.; Breazzano, S. P. Angew. Chem., Int. Ed. 2012, 51, 4080.
[15] Snyder, S. A.; Brill, Z. G. Org. Lett. 2011, 13, 5524.
[16] Snyder, S. A.; Gollner, A.; Chiriac, M. I. Nature 2011, 474, 461.
[17] Nicolaou, K. C.; Wu, T. R.; Kang, Q.; Chen, D. Y.-K. Angew. Chem., Int. Ed. 2009, 48, 3440.
[18] Nicolaou, K. C.; Kang, Q.; Wu, T. R.; Lim, C. S.; Chen, D. Y.-K. J. Am. Chem. Soc. 2010, 132, 7540.
[19] Kraus, G. A.; Kim, I. Org. Lett. 2003, 5, 1191.
[20] Kim, I.; Choi, J. Org. Biomol. Chem. 2009, 7, 2788.
[21] Kraus, G. A.; Gupta, V. Tetrahedron Lett. 2009, 50, 7180.
[22] Chen, D. Y.-K.; Kang, Q.; Wu, T. R. Molecules 2010, 15, 5909.
[23] Chiummento, L.; Funicello, M.; Lopardo, M. T.; Lupattelli, P.; Choppin, S.; Colobert, F. Eur. J. Org. Chem. 2012, 188.
[24] Chen, B.; Lu, J. P.; Xie, X. G.; She, X. G.; Pan, X. F. Chin. J. Org. Chem. 2006, 26, 1300 (in Chinese). (陈博, 卢江平, 谢新刚, 厍学功, 潘鑫复, 有机化学, 2006, 26, 1300.)
[25] Jeffery, J. L.; Sarpong, R. Tetrahedron Lett. 2009, 50, 1969.
[26] Jeffery, J. L.; Sarpong, R. Org. Lett. 2009, 11, 5450.
[27] Yang, Y.; Philips, D.; Pan, S. F. J. Org. Chem. 2011, 76, 1902.
[28] Lee, B. H.; Choi, Y. L.; Shin, S.; Heo, J.-N. J. Org. Chem. 2011, 76, 6611.
[29] Kerr, D. J.; Miletic, M.; Manchala, N.; White, J. M.; Flynn, B. L. Org. Lett. 2013, 15(16), 4118.
[30] Zhu, J.; Zhong, C.; Lu, H. F.; Li, G. Y.; Sun, X. Synlett 2008, 458.
[31] Zhong, C.; Zhu, J.; Chang, J.; Sun, X. Tetrahedron Lett. 2011, 52, 2815.
[32] Choi, Y. L.; Kim, B. T.; Heo, J.-N. J. Org. Chem. 2012, 77, 8762.
/
| 〈 |
|
〉 |
