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2022 , Vol. 42 >Issue 3: 758 - 769

DOI: https://doi.org/10.6023/cjoc202109030

综述与进展

黄烷酮的不对称合成研究进展

  • 王立花 ,
  • 公绪顺 ,
  • 雷婷 ,
  • 江世智
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  • a 大理大学药学院 云南大理 671000
    b 云南省滇西抗病原植物资源筛选研究重点实验室(培育) 云南大理 671000
† 共同第一作者

收稿日期: 2021-09-21

  修回日期: 2021-10-22

  网络出版日期: 2021-11-17

基金资助

云南省地方本科高校(部分)基础研究联合专项((2019FH001(-087))

收起

Research Progress on Asymmetric Synthesis of Flavanones

  • Lihua Wang ,
  • Xushun Gong ,
  • Ting Lei ,
  • Shizhi Jiang
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  • a College of Pharmacy, Dali University, Dali, Yunnan 671000
    b Yunnan Key Laboratory of Screening and Research on Anti-pathogenic Plant Resources from West Yunnan (Cultivation),Dali University, Dali, Yunnan 671000
† These authors contributed equally to this work.
* Corresponding author. E-mail:

Received date: 2021-09-21

  Revised date: 2021-10-22

  Online published: 2021-11-17

Supported by

Joint Special Fund Project for Basic Research of Local Undergraduate Universities (Part of) in Yunnan Province(2019FH001(-087))

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摘要

黄烷酮及其衍生物是一种重要的生物活性的天然产物, 在很多复杂的天然产物中存在该骨架结构, 具有广泛的生物活性, 对于黄烷酮的研究越来越得到重视. 手性黄烷酮其本身在植物当中是种重要的化学物质, 具有潜在的药用价值, 但其含量较少, 很多化学家致力于通过合成的方法来解决问题, 推动了对映体富集的黄烷酮类的制备, 但其制备过程存在一定的局限性, 对于一些复杂结构的黄烷酮类化合物仍很难实现, 这将是未来需要攻克的难题. 本文综述了近年来黄烷酮的不对称合成方法. 合成方法包括对羰基的还原、手性拆分、碳-碳键的形成、碳-杂键的形成及其他类型的合成方法.

关键词： 黄烷酮; 不对称合成; 综述

本文引用格式

王立花 , 公绪顺 , 雷婷 , 江世智 . 黄烷酮的不对称合成研究进展[J]. 有机化学, 2022 , 42(3) : 758 -769 . DOI: 10.6023/cjoc202109030

Abstract

Flavanones and their derivatives are important bioactivenatural products. The skeleton structure exists in many complex natural products and has a wide range of biological activities. The research on flavanones is getting more and more attention. Chiral flavanone itself is an important chemical substance in plants and has potential medicinal value, but its content is small. Many chemists are committed to solve the problem through synthetic methods, which promotes the preparation of enantiomerically enriched flavanones. The preparation process has certain limitations, but for some complex structures of flavanone compounds it is still difficult to achieve, This is going to be a problem to overcome in the future. The asymmetric synthesis methods of flavanones are reviewed in recent years. The synthesis methods include carbonyl reduction and chiral resolution of raceme, formation of carbon-carbon bonds, formation of carbon-heterobonds and other types of synthesis methods.

Key words： flavanones; asymmetric synthesis; review

参考文献

[1]
Veitch, N. C.; Grayer, R. J. Nat. Prod. Rep. 2011, 28, 1626.
[2]
Amado, N. G.; Fonseca, B. F.; Cerqueira, D. M.; Neto, V. M.; Abreu, J. G. Life Sci. 2011, 89(15-16), 545.
[3]
Crozier, A.; Jaganath, I. B.; Clifford, M. N. Nat. Prod. Rep. 2009, 26(8), 1001.
[4]
Nicolaou, K. C.; Pfefferkorn, J. A.; Roecker, A. J.; Cao, G. Q.; Barluenga, S.; Mitchell, H. J. J. Am. Chem. Soc. 2000, 122, 9939.
[5]
Marais, J. P. J.; Ferreira, D.; Slade, D. Phytochem. Lett. 2005, 66(18), 2145.
[6]
Gladiali, S.; Alberico, E. Chem. Soc. Rev. 2006, 35(3), 226.
[7]
Wang, D. S.; Chen, Q. A.; Lu, S. M.; Zhou, Y. G. Chem. Rev. 2011, 112(4), 2557.
[8]
Zhao, D. B.; Beiring, B.; Glorius, F. Angew. Chem., Int. Ed. 2013, 52(32), 8454.
[9]
Huddleston, R. R.; Krische, M. J. Org. Lett. 2003, 5(7), 1143.
[10]
Corey, E. J.; Mitra, R. B. J. Am. Chem. Soc. 1962, 84(15), 2938.
[11]
Rákosi, M.; Tökés, A. L.; Bognár, R. Tetrahedron Lett. 1970, 11(26), 2305.
[12]
Pellissier, H. Adv. Synth. Catal. 2011, 353(10), 1613.
[13]
Lemke, M. K.; Schwab, P.; Fischer, P.; Tischer, S.; Witt, M.; Noehringer, L.; Rogachev, V.; Jäger, A.; Kataeva, O.; Fröhlich, R.; Metz, P. Angew. Chem., Int. Ed. 2013, 52(44), 11651.
[14]
Patel, R.; Hanson, R.; Goswami, A. J. Ind. Microbiol. Biotechnol. 2003, 30, 252.
[15]
Lzumi, T.; Hino, T.; Kasahara, A. J. Chem. Soc., erkin Trans. 1 1992, (10), 1265.
[16]
Lzumi, T.; Suenaga, K. J. Heterocycl. Chem. 1997, 34, 1535.
[17]
Kasashi, K.; Kakuda, H.; Goto, M.; Kawabata, S.; Kometani, T. Tetrahedron: Asymmetry. 2003, 14(11), 1529.
[18]
Richard, G.; Button.; Peter, J.; Taylo J. Chem. Soc., erkin Trans. 2 1992, 1571.
[19]
Nibbs, A. E.; Scheidt, K. A. Eur. J. Inorg. 2012, 3, 449.
[20]
Solladié, G.; Gehrold, N.; Maignan, J. Tetrahedron: Asymmetry 1999, 10(14), 2739.
[21]
Chen, J.; Chen, J.; Lang, F.; Zhang, X. Y.; Cun, L. F.; Zhu, J.; Deng, J. G.; Liao, J. J. Am. Chem. Soc. 2010, 41(33), 4552.
[22]
Shintani, R.; Tsutsumi, Y.; Nagaosa, M.; Nishimura, T.; Hayashi, T. J. Am. Chem. Soc. 2009, 131(38), 13588.
[23]
Takaya, Y.; Ogasawara, M.; Hayashi, T.; Sakai, M.; Miyaura, N. J. Am. Chem. Soc. 1998, 120(22), 5579.
[24]
Shintani, R.; Takeda, M.; Nishimura, T.; Hayashi, T. Angew. Chem., Int. Ed. 2010, 49(23), 3969.
[25]
Han, F. Z.; Chen, G. H.; Zhang, X. Y.; Liao, J. Eur. J. Org. Chem. 2011, 16, 2928.
[26]
Korenaga, T.; Hayashi, K.; Akaki, Y.; Maenishi, R.; Sakai, T. Org. Lett. 2011, 13(8), 2022.
[27]
Cisak, A.; Mielczarek, C. J. Chem. Soc., erkin Trans 2. 1992, 1603.
[28]
Mino, T.; Hashimoto, M.; Uehara, K.; Naruse, Y.; Kobayashi, S.; Sakamoto, M.; Fujita, T. Tetrahedron Lett. 2012, 53(34), 4562.
[29]
He, Q. J.; So, C. M.; Bian, Z. X.; Hayashi, T.; Wang, J. Chem. Asian J. 2015, 10(3), 540.
[30]
Holder, J. C.; Marziale, A. N.; Gatti, M.; Mao, B.; Stoltz, B. M. Chemistry 2013, 19(1), 74.
[31]
Tamura, M.; Ogata, H.; Ishida, Y.; Takahashi, Y. Tetrahedron Lett. 2017, 58(40), 3808.
[32]
Meng, L.; Wang, J. ChemInform 2016, 47(5), 656.
[33]
Biddle, M. M.; Lin, M.; Scheidt, K. A. J. Am. Chem. Soc. 2007, 129(13), 3830.
[34]
Farmer, R. L.; Biddle, M. M.; Nibbs, A. E.; Huang, X.; Bergan, R. C.; Scheidt, K. A. ACS Med. Chem. Lett. 2010, 1(8), 400.
[35]
Wang, L. J.; Liu, X. H.; Dong, Z. H.; Fu, X.; Feng, X. M. Angew. Chem., Int. Ed. 2008, 47(45), 8670.
[36]
Feng, Z.; Zeng, M.; Xu, Q. L.; You, S. L. Sci. Bull. 2010, 55(17), 1723.
[37]
Wang, H. F.; Xiao, H.; Wang, X. W.; Zhao, G. Tetrahedron 2011, 67(30), 5389.
[38]
Dittmer, C.; Raabe, G. Hintermann Eur. J. Inorg 2007, 5886.
[39]
Miles, C. O.; Main, L.; Nicholson, B. K. Aust. J. Chem. 1989, 42, 1103.
[40]
Hintermann, L.; Dittmer, C. Eur. J. Inorg. 2012, 28, 5573.
[41]
Zhang, Y. L.; Wang, Y. Q. Tetrahedron Lett. 2014, 55(21), 3255.
[42]
Nising, C. F.; Bräse, S. Chem. Soc. Rev. 2012, 41, 988.
[43]
Reyes, E.; Talavera, G.; Vicario, J. L.; Badía, D.; Carrillo, L. Angew. Chem., nt. Ed. 2009, 48, 5701.
[44]
McDonald, B. R.; Nibbs, A. E.; Scheidt, K. A. Org. Lett. 2015, 17(1), 98.
[45]
Sharma, A.; Singh, M.; Rai, N. N.; Sawant, D. J. Org. Chem. 2013, 9, 1235.
[46]
Singh, A. K.; Mangawa, S. K.; Kumar, A.; Dixit, A. K.; Awasthi, S. K. ChemistrySelect 2017, 2(34), 11160.
[47]
Hodgetts, K. J. Tetrahedron Lett. 2001, 42, 3763.
[48]
Noda, Y.; Watanabe, M. Helv. Chim. Acta 2002, 85(10), 3473.
[49]
Wang, H. F.; Cui, H. F.; Chai, Z.; Li, P.; Zheng, C. W.; Yang, Y. Q.; Zhao, G. Chemistry 2009, 15(48), 13299.
[50]
Zhong, N. J; Liu, L.; Wang, D.; Chen, Y. J. Chem. Commun. (Camb.) 2013, 49(35), 3697.
[51]
Wen, G. F.; Su, Y. P.; Zhang, G. X.; Lin, Q. Q.; Zhu, Y. J.; Zhang, Q. Q.; Fang, X. Q. Org. Lett. 2016, 18(16), 3980.
[52]
Reddi, Y.; Sunoj, R. B. ACS Catal. 2015, 5(3), 1596.
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