Synthesis of Resveratrol, Piceatannol and Pinosylvin

doi:10.6023/cjoc201908014

Chinese Journal of Organic Chemistry ›› 2020, Vol. 40 ›› Issue (4): 1062-1067.DOI: 10.6023/cjoc201908014 Previous Articles Next Articles

白藜芦醇、白皮杉醇和赤松素的合成

张静静^a,b, 姚明^b, 李立^a,b, 桑大永^b, 熊航行^a,b, 刘生鹏^a

a 武汉工程大学化工与制药学院武汉 430205;
b 荆楚理工学院化工与药学院荆门 448000

收稿日期:2019-08-09 修回日期:2019-10-08 发布日期:2019-11-07
通讯作者: 姚明, 熊航行, 刘生鹏 E-mail:yaomingcep@jcut.edu.cn;731990153@qq.com;liuabss@163.com
基金资助:
湖北省高校优秀中青年科技创新团队（No.T201719）资助项目.

Synthesis of Resveratrol, Piceatannol and Pinosylvin

Zhang Jingjing^a,b, Yao Ming^b, Li Li^a,b, Sang Dayong^b, Xiong Hangxing^a,b, Liu Shengpeng^a

a School of Chemical Engineering and Pharmacy, Wuhan Institute of Technology, Wuhan 430205;
b College of Chemical Engineering and Pharmacy, Jingchu University of Technology, Jingmen 448000

Received:2019-08-09 Revised:2019-10-08 Published:2019-11-07
Supported by:
Project supported by the Science Technology Foundation for Creative Research Group of Hubei Department of Education (No. T201719).

1. 201062S.pdf(787KB)

Abstract

A convenient method for the practical synthesis of resveratrol, piceatannol and pinosylvin is described. Resveratrol, pinosylvin and piceatannol can be achieved through a simultaneous demethylation and isomerization process from stilbenes with the aid of aluminum and iodine. The overall yields of the reaction were 68%, 78% and 56% (based on aromatic aldehyde). The solvent of the reaction can be reused after filtered. At the same time, quantum chemical calculations and control experiments show that iodine radical may be the key factor leading to cis-trans isomerization of double bond in the process of demethylation.

Key words: resveratrol, stilbene, demethylation, Wittig reaction, cis-trans isomerisation

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Zhang Jingjing, Yao Ming, Li Li, Sang Dayong, Xiong Hangxing, Liu Shengpeng. Synthesis of Resveratrol, Piceatannol and Pinosylvin[J]. Chinese Journal of Organic Chemistry, 2020, 40(4): 1062-1067.

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[1] (a) Filippis, B. D.; Ammazzalorso, A.; Amoroso, R.; Giampietro, L. Drug Dev. Res. 2019, 80, 285.
(b) Keylor, M. H.; Matsuura, B. S.; Stephenson, C. R. Chem. Rev. 2015, 115, 8976.
(c) Si, J.-Y. Nat. Prod. Res. Dev. 1994, 6, 71(in Chinese). (斯建勇, 天然产物研究与开发, 1994, 6, 71.)
[2] Chen, G. H.; Webster, J. M.; Li, J. X.; Hu, K. J.; Zhu, J. WO 042231, 2001[Chem. Abstr. 2001, 135, 45986.]
[3] (a) Quideau, S.; Deffieux, D.; Pouysegu, L. Angew. Chem., Int. Ed. 2012, 51, 6824.
(b) Gao, H.; Zheng, X.; Qi, Y.; Wang S.; Wan C.; Rao, G.; Mao, Z. Chin. J. Org. Chem. 2018, 38, 648(in Chinese). (高慧, 郑喜, 祁燕, 王斯, 万春平, 饶高雄, 毛泽伟, 有机化学, 2018, 38, 648.)
[4] (a) Becker, K. B. Synthesis 1983, 341.
(b) Zhao, S.; Yu, Y.; Zhang, Y. Chin. J. Org. Chem. 2013, 33, 1851.
(c) Khan, Z. A.; Iqbal, A.; Shahzad, S. A. Mol. Diversity 2017, 21, 483.
[5] (a) Li, Q.; Shah, Z.; Qu, J. Kang, Y. J. Org. Chem. 2018, 83, 296.
(b) Srivastava, V. Catal. Lett. 2017, 147, 693.
(c) Zou, Y.; Huang, Q.; Huang, T.; Ni, Q.; Zhang, E.; Xu, T.; Yuan, M.; Li, J. Org. Biomol. Chem. 2013, 11, 6867.
(d) Gray, E. E.; Rabenold, L. E.; Goess, B. C. Tetrahedron Lett. 2011, 52, 6177.
(e) Sun, H.-Y.; Xiao, C.-F.; Cai, Y.-C.; Chen, Y.; Wei, W.; Liu, X.-K.; Lv, Z.-L.; Zou, Y. Chem. Pharm. Bull. 2010, 58, 1492.
(f) Alonso, F.; Riente, P.; Yus, M. Eur. J. Org. Chem. 2009, 34, 6034.
(g) Dong, D. J.; Li, H. H.; Tian, S. K. J. Am. Chem. Soc. 2010, 132, 5018.
(h) Alonso, F.; Riente, P.; Yus, M. Tetrahedron Lett. 2009, 50, 3070.
(i) McNulty, J.; Das, P. Eur. J. Org. Chem. 2009, 24, 4031.
(j) Roberti, M.; Pizzirani, D.; Simoni, D.; Rondanin, R.; Baruchello, R.; Bonora, C.; Buscemi, F.; Grimaudo, S.; Tolomeo, M. J. Med. Chem. 2003, 46, 3546.
(k) Ali, M. A.; Kondo, K.; Tsuda, Y. Chem. Pharm. Bull. 1992, 40, 1130.
[6] (a) Tian, J.; Yue, H.; Yang, P.; Sang, D. ChemistrySelect 2019, 4, 38.
(b) Sang, D.; Tian, J.; Tu, X.; He, Z.; Yao, M. Synthesis 2019, 51, 704.
(c) Sang, D.; Tu, X.; Tian, J.; He, Z.; Yao, M. ChemistrySelect 2018, 3, 10103.
(d) Sang, D.; Yao, M.; Tian, J.; Chen, X.; Zhan, H.; You, L. Synlett 2017, 28, 138.
[7] (a) Li, G.; Zou, Y.; Zhang, X. J. Chem. Res. 2007, 657.
(b) Sun, H.; Xiao, C.; Wei, W.; Chen, Y.; Lu, Z.; Zou, Y. Chin. J. Org. Chem. 2010, 30, 1574(in Chinese). (孙洪宜, 肖春芬, 魏文, 陈煜, 吕泽良, 邹永, 有机化学, 2010, 30, 1574.)
[8] (a) van Rossum, A. J. G.; de Bruin, A. H. M.; Nivard, R. J. F. J. Chem. Soc., Perkin Trans. 2 1975, 1036.
(b) Giacomelli, G.; Lardicci, L.; Saba, A. J. Chem. Soc., Perkin Trans. 1 1978, 314.
(c) Ali, M. A.; Tsuda, Y. Chem. Pharm. Bull. 1992, 40, 2842.
(d) Gaukroger, K.; Hadfield, J. A.; Hepworth, L. A.; Lawrence, N. J.; McGown, A. T. J. Org. Chem. 2001, 66, 8135.
(e) Hepprele, S. S.; Li, Q.; East, A. L. L. J. Phys. Chem. A 2005, 109, 10975.
(f) Deshpande, P. B.; Kumar, S.; Palanisamy, U.; Andrew, G. US 6844471, 2005.
(g) Li, Q.; Shah, Z.; Qu, J.; Kang, Y. J. Org. Chem. 2018, 83, 296.
(h) Settle, A. E.; Berstis, L.; Zhang, S.; Rorrer, N. A.; Hu, H.; Richards, R. M.; Beckham, G. T.; Crowley, M. F.; Vardon, D. R. ChemSusChem 2018, 11, 1768.
[9] (a) Das, M.; O'Shea, D. F. Org. Lett. 2016, 18, 336.
(b) Simoni, D.; Roberti, M.; Invidiata, F. P.; Aiello, E.; Aiello, S.; Marchetti, P.; Baruchello, R.; Eleopra, M.; Cristina, A. D.; Grimaudo, S.; Gebbia, N.; Crosta, L.; Dieli, F.; Tolomeo, M. Bioorg. Med. Chem. Lett. 2016, 16, 3245.
(c) Zaki, M. A.; Balachandran, P.; Khan, S.; Wang, M.; Mohammed, R.; Hetta, M. H.; Pasco, D. S.; Muhammad, I. J. Nat. Prod. 2013, 76, 679.
(d) Antonioletti, R.; Bonadies, F.; Ciammaichella, A.; Viglianti, A. Tetrahedron 2008, 64, 4644.
[10] (a) Sun, H.-Y.; Xiao, C.-F.; Cai, Y.-C.; Chen, Y.; Wei, W.; Liu, X.-K.; Lv, Z.-L.; Zou, Y. Chem. Pharm. Bull. 2010, 58, 1492.
(b) Jayatilake, G. S.; Jayasuriya, H.; Lee, E. S.; Koonchanok, N. M.; Geahlen, R. L.; Ashendel, C. L.; McLaughlin, J. L.; Chang, C. J. J. Nat. Prod. 1993, 56, 1805.
(c) Uzura, S.; Sekine-Suzuki, E.; Nakanishi, I.; Sonoda, M.; Tanimori, S. Bioorg. Med. Chem. Lett. 2016, 26, 3886.

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白藜芦醇、白皮杉醇和赤松素的合成

Synthesis of Resveratrol, Piceatannol and Pinosylvin

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