综述与进展

酰基自由基化学在天然产物全合成中的应用

  • 谢应 ,
  • 付绍敏 ,
  • 刘波
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  • a 四川轻化工大学化学与环境工程学院 四川自贡 643000
    b 四川大学化学学院 绿色化学与技术教育部重点实验室 成都 610064

收稿日期: 2024-09-24

  修回日期: 2024-11-28

  网络出版日期: 2024-12-20

基金资助

国家自然科学基金(21925106); 国家自然科学基金(21921002)

Application of Acyl Radical in Total Synthesis of Natural Products

  • Ying Xie ,
  • Shaomin Fu ,
  • Bo Liu
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  • a School of Chemistry and Environmental Engineering, Sichuan University of Science & Engineering, Zigong, Sichuan 643000
    b Key Laboratory of Green Chemistry & Technology of Ministry of Education, College of Chemistry, Sichuan University, Chengdu, 610064

Received date: 2024-09-24

  Revised date: 2024-11-28

  Online published: 2024-12-20

Supported by

National Natural Science Foundation of China(21925106); National Natural Science Foundation of China(21921002)

摘要

酰基自由基具有独特的结构特征和高反应活性, 受到有机合成化学家的广泛关注. 近年来, 随着其来源和引发方式的不断创新, 酰基自由基在各种化学转化中的应用日益广泛; 特别是在天然产物合成后期的关键步骤中, 酰基自由基因的较小位阻以及不易发生金属介导的β-消除反应等优势, 成为兼容多种官能团行之有效的策略之一. 此文综述了近年来通过酰基自由基化学作为关键步骤在复杂天然产物合成中的应用.

本文引用格式

谢应 , 付绍敏 , 刘波 . 酰基自由基化学在天然产物全合成中的应用[J]. 有机化学, 2025 , 45(3) : 852 -861 . DOI: 10.6023/cjoc202409033

Abstract

Acyl radicals have received extensive attention from organic synthetic chemists due to their unique structural features and high reactivity. In recent years, with the continuous innovation of their acyl sources and initiation modes, acyl radicals have been widely used in various chemical transformations. Especially in the critical step of the late stage of natural product synthesis, acyl radicals have become one of the effective and important strategies compatible with a wide range of functional groups due to the advantages of their smaller site resistance and less susceptibility to metal-mediated β-elimination reactions. Application of acyl radicals as a key step in the synthesis of natural products is summarized.

参考文献

[1]
(a) Duncton, M. A. J. MedChemComm 2011, 2, 1135.
[1]
(b) Liu, Y.-L.; Ouyang, Y.-J.; Zheng, H.; Liu, H.; Wei, W.-T. Chem. Commun. 2021, 57, 6111.
[1]
(c) Wu, Y. C.; Yu, J. T. Chin. J. Org. Chem. 2022, 42, 3606. (in Chinese)
[1]
(吴业春, 于金涛, 有机化学, 2022, 42, 3606.)
[2]
(a) Ruan, L. H.; Zhang, C. X.; Zhang, X. X.; Sun, J. Chin. J. Org. Chem. 2018, 38, 3155. (in Chinese)
[2]
(阮利衡, 陈春欣, 张晓欣, 孙京, 有机化学, 2018, 38, 3155.)
[2]
(b) Chatgilialoglu, C.; Crich, D.; Komatsu, M.; Ryu, I. Chem. Rev. 1999, 99, 1991.
[2]
(c) Banerjee, A.; Lei, Z.; Ngai, M.-Y. Synthesis 2019, 51, 303.
[3]
Faltings, K. Ber. 1939, 72B, 1207.
[4]
Ryu, I.; Kusano, K.; Ogawa, A.; Kambe, N.; Sonoda, N. J. Am. Chem. Soc. 1990, 112, 1295.
[5]
Falzon, C. T.; Ryu, I.; Schiesser, C. H. Chem. Commun. 2002, 2338.
[6]
(a) Matsubara, H.; Falzon, C. T.; Ryu, I.; Schiesser, C. H. Org. Biomol. Chem. 2006, 4, 1920.
[6]
(b) Schiesser, C. H.; Wille, U.; Matsubara, H.; Ryu, I. Acc. Chem. Res. 2007, 40, 303.
[7]
Tojino, M.; Otsuka, N.; Fukuyama, T.; Matsubara, H.; Ryu, I. J. Am. Chem. Soc. 2006, 128, 7712.
[8]
Fukuyama, T.; Nishitani, S.; Inouye, T.; Morimoto, K.; Ryu, I. Org. Lett. 2006, 8, 1383.
[9]
Kondo, T.; Sone, Y.; Tsuji, Y.; Watanabe, Y. J. Organomet. Chem. 1994, 473, 163.
[10]
Boger, D. L.; Hong, J. J. Am. Chem. Soc. 2001, 123, 8515.
[11]
(a) Fürstner, A.; Weintritt, H. J. Am. Chem. Soc. 1998, 120, 2817.
[11]
(b) Fürstner, A.; Weintritt, H. J. Am. Chem. Soc. 1997, 119, 2944.
[12]
Wong, L. S. M.; Sherburn, M. S. Org. Lett. 2003, 5, 3603.
[13]
Bennasar, M. L.; Roca, T.; Ferrando, F. J. Org. Chem. 2006, 71, 1746.
[14]
Bennasar, M. L.; Roca, T.; Ferrando, F. Org. Lett. 2006, 8, 561.
[15]
Bennasar, M. L.; Roca, T.; García-Díaz, D. J. Org. Chem. 2008, 73, 9033.
[16]
Zaimoku, H.; Taniguchi, T.; Ishibashi, H. Org. Lett. 2012, 14, 1656.
[17]
Zhang, L.; Koreeda, M. Org. Lett. 2004, 6, 537.
[18]
Inoue, M.; Ishihara, Y.; Yamashita, S.; Hirama, M. Org. Lett. 2006, 8, 5801.
[19]
Johnston, L. J.; Lusztyk, J.; Wayner, D. D. M.; Abeywickreyma, A. N.; Beckwith, A. L. J.; Scaiano, J. C.; Ingold, K. U. J. Am. Chem. Soc. 1985, 107, 4594.
[20]
Sato, S.; Fukuda, Y.; Ogura, Y.; Kwon, E.; Kuwahara, S. Angew. Chem., Int. Ed. 2017, 56, 10911.
[21]
Giroux, S.; Corey, E. J. Org. Lett. 2008, 10, 801.
[22]
Grélaud, S.; Lusseau, J.; Landais, Y. Eur. J. Org. Chem. 2017, 2017, 1323.
[23]
Li, X.; Zhang, Z.; Fan, H.; Miao, Y.; Tian, H.; Gu, Y.; Gui, J. J. Am. Chem. Soc. 2021, 143, 4886.
[24]
Crich, D.; Yao, Q. J. Org. Chem. 1996, 61, 3566.
[25]
Ju, W.; Wang, X.; Tian, H.; Gui, J. J. Am. Chem. Soc. 2021, 143, 13016.
[26]
Yamada, K.-I.; Sato, T.; Hosoi, M.; Yamamoto, Y.; Tomioka, K. Chem. Pharm. Bull. 2010, 58, 1511.
[27]
Hanessian, S.; Ninkovic, S. J. Org. Chem. 1996, 61, 5418.
[28]
Chen, C.-M.; Shiao, H.-Y.; Uang, B.-J.; Hsieh, H.-P. Angew. Chem., nt. Ed. 2018, 57, 15572.
[29]
Yoshikai, K.; Hayama, T.; Nishimura, K.; Yamada, K.-I.; Tomioka, K. J. Org. Chem. 2005, 70, 681.
[30]
Uwamori, M.; Osada, R.; Sugiyama, R.; Nagatani, K.; Nakada, M. J. Am. Chem. Soc. 2020, 142, 5556.
[31]
Yokoe, H.; Mitsuhashi, C.; Matsuoka, Y.; Yoshimura, T.; Yoshida, M.; Shishido, K. J. Am. Chem. Soc. 2011, 133, 8854.
[32]
Honda, T.; Favaloro, F. G., Jr.; Janosik, T.; Honda, Y.; Suh, N.; Sporn, M.; Gribble, G. W. Org. Biomol. Chem. 2003, 1, 4384.
[33]
Kang, G.; Han, S, J. Am. Chem. Soc. 2022, 144, 8932.
[34]
Chen, C.-M.; Lin, S.-K.; Hsieh, C.-T.; Reddy, J. S.; Teoh, Y. N.; Cheng, M.-J.; Hsieh, H.-P. Org. Lett. 2023, 25, 7757.
[35]
Le, S.; Li, J.; Feng, J.; Zhang, Z.; Bai, Y.; Yuan, Z.; Zhu, G. Nat. Commun. 2022, 13, 4734.
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