Study on the Total Synthesis of Resveratrol Dimers Quadrangularin A and Pallidol

doi:10.6023/cjoc202001031

Chinese Journal of Organic Chemistry ›› 2020, Vol. 40 ›› Issue (6): 1571-1577.DOI: 10.6023/cjoc202001031 Previous Articles Next Articles

白藜芦醇二聚体Quadrangularin A和Pallidol合成方法学研究

韩吉来^a, 唐美麟^a,c, 孙逊^a,b

a 复旦大学药学院天然药物系上海 201203;
b 复旦大学中西医结合研究所上海 200040;
c 复旦大学生物医学研究院上海 200433

收稿日期:2020-01-23 修回日期:2020-03-13 发布日期:2020-04-10
通讯作者: 孙逊 E-mail:sunxunf@shmu.edu.cn
基金资助:
国家自然科学基金（No.81673297）、上海市科委基金（No.17431902500）和中国博士后基金（No.2019M651384）资助项目.

Study on the Total Synthesis of Resveratrol Dimers Quadrangularin A and Pallidol

Han Jilai^a, Tang Meilin^a,c, Sun Xun^a,b

a Department of Natural Medicine, School of Pharmacy, Fudan University, Shanghai 201203;
b The Institutes of Integrative Medicine of Fudan University, Shanghai 200040;
c Institutes of Biomedical Sciences, Fudan University, Shanghai 200433

Received:2020-01-23 Revised:2020-03-13 Published:2020-04-10
Supported by:
Project supported by the National Natural Science Foundation of China (No. 81673297), the Shanghai Committee of Science and Technology (No. 17431902500), and the China Postdoctoral Science Foundation (No. 2019M651384).

1. 201571S.pdf(726KB)

Abstract

This paper has focused on developing a novel methodology for the total synthesis of quadrangularin A (3) and pallidol (4). These two resveratrol dimers have been obtained from the inexpensive materials of 3,5-dimethoxybenzaldehyde (5) and 3,5-dimethoxybenzaldehyde (6) within 9 steps and 11 steps with total yields of 2.6% and 1.3%, respectively. The stilbene skeleton constructed by two symmetric or asymmetric aromatic rings (A and B) has been synthesized simply through Knoevenagel reaction under mild conditions with yield of more than 98%, which expanded the diversity of stilbene skeleton (7), and addressed the problems of limited expansion of asymmetric structure, low yield and complex operation. In addition, the key intermediate of 4-enaldehyde skeleton structure (9) could be used to construct aromatic rings of C and D efficiently, which has thrown light on the expansion of resveratrol dimers with aromatic ring A, B, C and D in diversity structure. All the intermediates and natural products have been characterized by ¹H NMR, ¹³C NMR, and HRMS.

Key words: resveratrol oligomer, Friedel-Crafts reaction, Grignard regent addition reaction, total synthesis

Cite this article

Han Jilai, Tang Meilin, Sun Xun. Study on the Total Synthesis of Resveratrol Dimers Quadrangularin A and Pallidol[J]. Chinese Journal of Organic Chemistry, 2020, 40(6): 1571-1577.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[1] Huang, K. S.; Lin, M.; Yu, L N.; Kong, M. Tetrahedron 2000, 56, 1321.
[2] Huang, K S.; Lin, M; Cheng, G. Phytochemistry 2001, 58, 357.
[3] Ito, J.; Takaya, Y.; Oshima, Y.; Niwa, M. Tetrahedron 1999, 55, 2529.
[4] Li, W. W.; Ding, L.; Li, B.; Chen, Y. Z. Phytochemistry 1996, 42, 1163.
[5] Cichewicz, R. H.; Kouzi, S. A.; Hamann, M. T. J. Nat. Prod. 2000, 63, 29.
[6] He, S.; Lu, Y.; Wu, B.; Pan, Y. J. Chromatogr. A 2007, 1151, 175.
[7] Li, W.; Teng, L.; Yang, Y.; Yang, Y. Chin. J. Org. Chem. 2013, 33, 2443(in Chinese). (李文玲, 吕腾, 杨玉华, 有机化学, 2013, 33, 2443.)
[8] Keylor, M. H.; Matsuura, B. S.; Stephenson, C. R. J. Chem. Rev. 2015, 115, 8976
[9] Davin, B. L.; Wang, H.-B. Science 1997, 275(5298), 362.
[10] Kim, K. W.; Smith, C. A.; Daily, M. D.; Cort, J. R.; Davin, L. B.; Lewis, N. G. J. Biol. Chem. 2009, 290, 1308.
[11] Sako, M.; Hosokawa, H.; Ito, T.; Iinuma, M. J. Org. Chem. 2004, 69, 2598.
[12] Nicotra, S.; Cramarossa, M. R.; Mucci, A.; Pagnoni, U. M.; Riva, S.; Forti, L. Tetrahedron 2004, 60, 595.
[13] Li, W. L.; Li, H.; Li, Y.; Angew. Chem., Int. Ed. 2006, 45, 7609.
[14] Li, W. L.; Li., H. F.; Luo, Y. L.; Yang, Y.; Wang, N. Synlett 2010, 1247.
[15] Matsuura, B. S.; Keylor, M. H.; Li, B.; Lin, Y.; Allison, S.; Pratt, D. A.; Stephenson, C. R. J. Angew. Chem., Int. Ed. 2015, 54, 3754.
[16] Keylor, M. H.; Matsuura, B. S.; Griesser, M.; Chauvin, J. P. R.; Harding, R. A.; Kirillova, M. S.; Zhu, X.; Fischer, O. J.; Pratt, D. A.; Stephenson, C. R. J. Science 2016, 354, 1260.
[17] Snyder, S. A.; Breazzano, S. P.; Ross, A. G.; Lin, Y.; Zografos, A. L. J. Am. Chem. Soc. 2009, 131, 1753
[18] Snyder, S. A.; Gollner, A.; Chiriac, M. I. Nature 2011, 474, 461
[19] Snyder, S. A.; Wright, N. E.; Pflueger, J. J.; Breazzano, S. P. Angew. Chem. 2011, 123, 8788
[20] Snyder, S. A.; Thomas, S. B.; Dr. Mayer, A. C.; Breazzano, S. P. Angew. Chem. 2007, 51, 4080
[21] Snyder, S. A.; Zografos, A. L.; Lin, Y. Angew. Chem. 2007, 119, 8334.
[22] Snyder, S. A.; Zografos, A. L.; Lin, Y. Angew. Chem., Int. Ed. 2007, 46, 818.
[23] Snyder, S. A.; Brill, Z. G. Org. Lett. 2011, 13, 5524
[24] Wright, N. E., Snyder, S. A. Angew. Chem., Int. Ed. 2014, 53, 3409.
[25] Nicolaou, K. C.; Wu, T. R.; Kang, Q.; Chen, D. Y. K. Angew. Chem., Int. Ed. 2009, 48, 3440.
[26] Kerr, D. J.; Miletic, M.; Manchala, N.; White, J. M.; Flynn, B. L. Org. Lett. 2013, 15, 4118.
[27] Soldi, C.; Lamb, K. N.; Squitieri, R. A.; González-López, M.; Di Maso, M. J.; Shaw, J. T. J. Am. Chem. Soc. 2014, 136, 15142.
[28] Kraus, G. A.; Gupta, V. Tetrahedron Lett. 2009, 50, 7180.
[29] Sun, X.; Izumi, K. J.; Hu, C. Q.; Lin, G. Q. Chin. J. Chem. 2006, 24, 430.
[30] Sun, X.; Zhu, J.; Zhong, C.; Izumi, K. J.; Zhang, C. Chin. J. Chem. 2010, 25, 1866.
[31] Zhu, J.; Zhong, C.; Lu, H. F.; Li, G. Y.; Sun, X. Synlett 2008, 458.
[32] Chen, Z.; Zhu, J.; Chang, J.; Sun, X. Tetrahedron Lett. 2011, 52, 2815.
[33] Meyers, M. J. Med. Chem. 2001, 44, 4230.
[34] Yoo, J.; Dence, C. S.; Sharp, T. L.; Katzenellenbogen, J. A.; Welch, M. J. Med. Chem. 2005, 48, 6366
[35] Tang, M.-L.; Peng, P.; Liu, Z.-Y.; Zhang, J.; Yu, J.-M.; Sun, X. Chem.-Eur. J. 2016, 22, 14535.
[36] Jepsen, T. H,;Thomas, S. B.; Lin, Y.; Stathakis, C. I.; de Miguel, I.; Snyder, S. A. Angew. Chem., Int. Ed. 2014, 53, 6747.

白藜芦醇二聚体Quadrangularin A和Pallidol合成方法学研究

Study on the Total Synthesis of Resveratrol Dimers Quadrangularin A and Pallidol

PDF

Supporting Info.

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Xingzhou Liu, Mingjia Yu, Jianhua Liang. Research Progress on the Synthesis of Protoberberine Skeleton and Its Anti-inflammatory Activity [J]. Chinese Journal of Organic Chemistry, 2023, 43(4): 1325-1340.
[2]	Jingping Hu, Wenqing Chen, Yuyang Jiang, Jing Xu. Synthesis of Tetracyclic Core Structure of Daphnezomines A and B [J]. Chinese Journal of Organic Chemistry, 2023, 43(1): 171-177.
[3]	Xiangkai Kong, Yipeng Zhang, Lingjing Dang, Wen Chen, Hongbin Zhang. Research Progress in Synthesis of Indole Alkaloids Vindoline and Vindorosine [J]. Chinese Journal of Organic Chemistry, 2022, 42(9): 2728-2744.
[4]	Ran Gao, Weisheng Tian. Synthesis of Azedarachol and 2α,3α,20R-Trihydroxypregnane-16β-methacrylate [J]. Chinese Journal of Organic Chemistry, 2022, 42(8): 2521-2526.
[5]	Mengmeng Xu, Quan Cai. Progress of Catalytic Asymmetric Diels-Alder Reactions of 2-Pyrones [J]. Chinese Journal of Organic Chemistry, 2022, 42(3): 698-713.
[6]	Jun Zhao, Jian Xiao, Yawen Wang, Yu Peng. Advances on the Synthesis of Natural Products with Dihydrobenzofuran Skeleton via Oxidative [3+2] Cycloadditions [J]. Chinese Journal of Organic Chemistry, 2021, 41(8): 2933-2945.
[7]	Minxin Li, Qiuping Zou, Wenrong Du, Jinchun Gao, Yanping Li, Zewei Mao. Total Synthesis and Anti-inflammatory Evaluation of Dorsmerunin A [J]. Chinese Journal of Organic Chemistry, 2021, 41(8): 3292-3296.
[8]	Jian Xiao, Yu Peng, Wei-Dong Z. Li. Advances on the Total Synthesis of Sesquiterpenoid Alkaloid Dendrobine [J]. Chinese Journal of Organic Chemistry, 2021, 41(7): 2636-2649.
[9]	Xifei Yan, Jianfeng Zheng, Wei-Dong Z. Li. Studies on the Chemical Synthesis of Natural Drugs Berberine [J]. Chinese Journal of Organic Chemistry, 2021, 41(6): 2217-2227.
[10]	Junwei Zhang, Hao Wu, Weixin Zhang, Liming Wang, Ying Jin. Enantioselective Friedel-Crafts Reaction of Indoles with Isatins Catalyzed by Cinchona Alkaloid Silyl Ether Derivative [J]. Chinese Journal of Organic Chemistry, 2021, 41(3): 1187-1192.
[11]	Ding Ma, Junli Ao, Naifeng Hu, Guangxin Liang. Progress in Biological Activity and Synthesis of Nematode Hatching Pheromone Glycinoeclepin A [J]. Chinese Journal of Organic Chemistry, 2021, 41(2): 553-566.
[12]	Gang Yang, Xiangyu Feng, Congcong Han, Yang Chen, Shuzhong He. Synthesis of the ABC Ring System of Wallichanol Natural Product [J]. Chinese Journal of Organic Chemistry, 2021, 41(2): 726-730.
[13]	Feifan Li, Jin Qu. Synthesis of Aryl or Heteroaryl C-Nucleosides by Direct Coupling of a Carbohydrate Moiety with a Preformed Aglycon Unit [J]. Chinese Journal of Organic Chemistry, 2021, 41(10): 3948-3964.
[14]	Lu Guo, Pingping Tang. Recent Advance in the Synthesis of Natural Products of Schisandra Triterpenoid [J]. Chinese Journal of Organic Chemistry, 2021, 41(10): 3816-3825.
[15]	Zhiyu Hu, Guofang Jiang, Zhiqiang Zhu, Bozhen Gong, Zongbo Xie, Zhanggao Le. One-Pot Domino Henry-Friedel-Crafts Alkylation Reaction in Deep Eutectic Solvent [J]. Chinese Journal of Organic Chemistry, 2021, 41(1): 325-332.