REVIEWS

Application of Acyl Radical in Total Synthesis of Natural Products

  • Ying Xie ,
  • Shaomin Fu ,
  • Bo Liu
Expand
  • 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)

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.

Cite this article

Ying Xie , Shaomin Fu , Bo Liu . Application of Acyl Radical in Total Synthesis of Natural Products[J]. Chinese Journal of Organic Chemistry, 2025 , 45(3) : 852 -861 . DOI: 10.6023/cjoc202409033

References

[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.
Outlines

/