综述与进展

手性螺环缩酮化合物的不对称催化合成研究进展

  • 闫辉 ,
  • 张曼 ,
  • 李琳 ,
  • 胡腾 ,
  • 杨武林
展开
  • 华东理工大学药学院 上海市化学生物学重点实验室 上海 200237

收稿日期: 2022-05-01

  修回日期: 2022-06-13

  网络出版日期: 2022-06-29

基金资助

国家自然科学基金(22171081)

Advances in the Catalytic Asymmetric Synthesis of Chiral Spiroketals

  • Hui Yan ,
  • Man Zhang ,
  • Lin Li ,
  • Teng Hu ,
  • Wulin Yang
Expand
  • Shanghai Key Laboratory of Chemical Biology & School of Pharmacy, East China University of Science and Technology, Shanghai 200237

Received date: 2022-05-01

  Revised date: 2022-06-13

  Online published: 2022-06-29

Supported by

National Natural Science Foundation of China(22171081)

摘要

螺环缩酮是一类结构独特的螺环骨架, 其作为核心结构单元广泛存在于天然产物、生物活性分子和优势手性配体中, 发展其高效的合成方法一直以来都是有机化学领域的研究热点. 尤其是近10年来, 手性螺环缩酮化合物的催化不对称合成取得了重要突破. 根据反应类型划分, 总结了手性螺环缩酮化合物的催化不对称合成研究进展, 并对该领域的研究前景进行了展望.

本文引用格式

闫辉 , 张曼 , 李琳 , 胡腾 , 杨武林 . 手性螺环缩酮化合物的不对称催化合成研究进展[J]. 有机化学, 2022 , 42(11) : 3640 -3657 . DOI: 10.6023/cjoc202205001

Abstract

As an unique spiro skeleton, spiroketals are ubiquitous motifs in many natural products, biologically active molecules, and privileged chiral ligands. The development of efficient synthetic methods for the preparation of spiroketals has long been a hot research topic in organic synthesis. In particular, the remarkable advances regarding the catalytic asymmetric synthesis of chiral spiroketals have been achieved over the past decade. The progress in the field of catalytic asymmetric synthesis of chiral spiroketals is summarized according to the reaction types. The future development direction of this field is also prospected.

参考文献

[1]
(a) Zhu, S.-F.; Zhou, Q.-L. In Privileged Chiral Ligands and Catalysts, Ed.: Zhou, Q.-L., Wiley-VCH, Weinheim, 2011, pp. 137-170.
[1]
(b) Ding, K.; Han, Z.; Wang, Z. Chem. Asian J. 2009, 4, 32.
[1]
(c) Ramon, R. Chem. Soc. Rev. 2012, 41, 1060.
[2]
(a) Perron, F.; Albizati, K. F. Chem. Rev. 1989, 89, 1617.
[2]
(b) Wilsdorf, M.; Reissig, H. U. Angew. Chem., Int. Ed. 2012, 51, 9486.
[3]
(a) Aho, J. E.; Pihko, P. M.; Rissa, T. K. Chem. Rev. 2005, 105, 4406.
[3]
(b) Sperry, J.; Wilson, Z. E.; Rathwell, D. C. K.; Brimble, M. A. Nat. Prod. Rep. 2010, 27, 1117.
[3]
(c) Atkinson, D. J.; Brimble, M. A. Nat. Prod. Rep. 2015, 32, 811.
[3]
(d) Zhang, F.-M.; Zhang, S.-Y.; Tu, Y.-Q. Nat. Prod. Rep. 2018, 35, 75.
[3]
(e) Gillard, R. M.; Brimble, M. A. Org. Biomol. Chem. 2019, 17, 8272.
[4]
Liu, W.-Z.; Ma, L.-Y.; Liu, D.-S.; Huang, Y.-L.; Wang, C.-H.; Shi, S.-S.; Pan, X.-H.; Song, X.-D.; Zhu, R.-X. Org. Lett. 2014, 16, 90.
[5]
Fujimoto, H.; Nozawa, M.; Okuyama, E.; Ishibashi, M. Chem. Pharm. Bull. 2002, 50, 330.
[6]
Li, J.; Li, L.; Si, Y.; Jiang, X.; Guo, L.; Che, Y. Org. Lett. 2011, 13, 2670.
[7]
Stierle, A. A.; Stierle, D. B.; Kelly, K. J. Org. Chem. 2006, 71, 5357;
[8]
Zhuravleva, O. I.; Sobolevskaya, M. P.; Afiyatullov, S. S.; Kirichuk, N. N.; Denisenko, V. A.; Dmitrenok, P. S.; Yurchenko, E. A.; Dyshlovoy, S. A. Mar. Drugs 2014, 12, 5930.
[9]
Namikoshi, M.; Kobayashi, H.; Yoshimoto, T.; Meguro, S. Chem. Lett. 2000, 29, 308.
[10]
(a) Twiner, M. J.; Doucette, G. J.; Pang, Y.; Fang, C.; Forsyth, C. J.; Miles, C. O. Mar. Drugs 2016, 14, 207.
[10]
(b) Fu, L.-L.; Zhao, X.-Y.; Ji, L.-D.; Xu, J. Toxicon 2019, 160, 1.
[11]
Reddy, C. R.; Srikanth, B.; Dilipkumar, U.; Rao, K. M. V.; Jagadeesh, B. Eur. J. Org. Chem. 2013, 525.
[12]
Trost, B. M.; Weiss, A. H. Angew. Chem., Int. Ed. 2007, 46, 7664.
[13]
Uckun, F. M.; Mao, C.; Vassilev, A. O.; Huang, H.; Jan, S.-T. Bioorg. Med. Chem. Lett. 2000, 10, 541.
[14]
Scheepstra, M.; Andrei, S. A.; Unver, M. Y.; Hirsch, A. K. H.; Leysen, S.; Ottmann, C.; Brunsveld, L.; Milroy, L.-G. Angew. Chem., Int. Ed. 2017, 56, 5480.
[15]
(a) Wang, X.; Ding, K. Chin. J. Chem. 2018, 36, 899.
[15]
(b) Wang, X.; Han, Z.; Wang, Z.; Ding, K. Acc. Chem. Res. 2021, 54, 668.
[15]
(c) Li, J.; Chen, G.; Wang, Z.; Zhang, R.; Zhang, X.; Ding, K. Chem. Sci. 2011, 2, 1141.
[16]
(a) Argüelles, A. J.; Sun, S.; Budaitis, B. G.; Nagorny, P. Angew. Chem., Int. Ed. 2018, 57, 5325.
[16]
(b) Huang, J.; Hong, M.; Wang, C.-C.; Kramer, S.; Lin, G.-Q.; Sun, X.-W. J. Org. Chem. 2018, 83, 12838.
[17]
(a) Rizzacasa, M. A.; Pollex, A. Org. Biomol. Chem. 2009, 7, 1053.
[17]
(b) Raju, B. R.; Saikia, A. K. Molecules 2008, 13, 1942.
[17]
(c) Sperry, J.; Liu, Y.-C.; Brimble, M. A. Org. Biomol. Chem. 2010, 8, 29.
[17]
(d) Palmes, J. A.; Aponick, A. Synthesis 2012, 44, 3699.
[17]
(e) Quach, R.; Chorley, D. F.; Brimble, M. A. Org. Biomol. Chem. 2014, 12, 7423.
[17]
(f) Quach, R.; Furkert, D. P.; Brimble, M. A. Org. Biomol. Chem. 2017, 15, 3098.
[18]
?ori?, I.; List, B. Nature 2012, 483, 315.
[19]
(a) Sun, Z.; Winschel, G. A.; Borovika, A.; Nagorny, P. J. Am. Chem. Soc. 2012, 134, 8074.
[19]
(b) Khomutnyk, Y. Y.; Argu?elles, A. J.; Winschel, G. A.; Sun, Z.; Zimmerman, P. M.; Nagorny, P. J. Am. Chem. Soc. 2016, 138, 444.
[20]
Wang, X.; Han, Z.; Wang, Z.; Ding, K. Angew. Chem., Int. Ed. 2012, 51, 936;
[21]
Wang, X.; Guo, P.; Wang, X.; Wang, Z.; Ding, K. Adv. Synth. Catal. 2013, 355, 2900.
[22]
Liu, N.; Zhu, W.; Yao, J.; Yin, L.; Lu, T.; Dou, X. ACS Catal. 2020, 10, 2596.
[23]
Han, X.; Floreancig, P. E. Angew. Chem., Int. Ed. 2014, 53, 11075.
[24]
Rexit, A. A.; Mailikezati, M. Tetrahedron Lett. 2015, 56, 2651.
[25]
Yoneda, N.; Fukata, Y.; Asano, K.; Matsubara, S. Angew. Chem., Int. Ed. 2015, 54, 15497.
[26]
Xue, J.; Zhang, H.; Tian, T.; Yin, K.; Liu, D.; Jiang, X.; Li, Y.; Jin, X.; Yao, X. Adv. Synth. Catal. 2016, 358, 370.
[27]
Hamilton, J. Y.; Ro?ssler, S. L.; Carreira, E. M. J. Am. Chem. Soc. 2017, 139, 8082.
[28]
R?ssler, S. L.; Schreib, B. S.; Ginterseder, M.; Hamilton, J. Y.; Carreira, E. M. Org. Lett. 2017, 19, 5533.
[29]
Midya, A.; Maity, S.; Ghorai, P. Chem. Eur. J. 2017, 23, 11216.
[30]
Roy, T. K.; Gorad, S. S.; Ghorai, P. Org. Lett. 2022, 24, 1889.
[31]
Reddy, R. R.; Panda, S.; Ghorai, P. J. Org. Chem. 2019, 84, 5357.
[32]
Zheng, T.; Wang, X.; Ng, W.-H.; Tse, Y.-L. S.; Yeung, Y.-Y. Nat. Catal. 2020, 3, 993.
[33]
Xu, S.; Huang, A.; Yang, Y.; Wang, Y.; Zhang, M.; Sun, Z.; Zhao, M.; Wei, Y.; Li, G.; Hong, L. Org. Lett. 2022, 24, 2978.
[34]
Hilby, K. M.; Denmark, S. E. J. Org. Chem. 2021, 86, 14250.
[35]
Audrain, H.; Thorhauge, J.; Hazell, R. G.; J?rgensen, K.-A. J. Org. Chem. 2000, 65, 4487.
[36]
Yu, S.; Gao, L.; Yan, Y.; Yin, Z.; Shang, Y. Chin. J. Org. Chem. 2021, 41, 582. (in Chinese)
[36]
( 余述燕, 高丽宏, 闫溢哲, 尹志刚, 商永嘉, 有机化学 2021, 41, 582.)
[37]
Wu, H.; He, Y.-P.; Gong, L.-Z. Org. Lett. 2013, 15, 460.
[38]
Cala, L.; Mendoza, A.; Fa?anás, F. J.; Rodríguez, F. Chem. Commun. 2013, 49, 2715.
[39]
(a) Wang, X.; Dong, S.; Yao, Z.; Feng, L.; Daka, P.; Wang, H.; Xu, Z. Org. Lett. 2014, 16, 22.
[39]
(b) Liang, M.; Zhang, S.; Jia, J.; Tung, C.-H.; Wang, J.; Xu, Z. Org. Lett. 2017, 19, 2526.
[39]
(c) Teng, Q.; Qi, J.; Zhou, L.; Xu, Z.; Tung, C.-H. Org. Chem. Front. 2018, 5, 990.
[39]
(d) Mao, W.; Lin, S.; Zhang, L.; Lu, H.; Jia, J.; Xu, Z. Org. Chem. Front. 2020, 7, 856.
[40]
Li, J.; Lin, L.; Hu, B.; Lian, X.; Wang, G.; Liu, X.; Feng, X. Angew. Chem., Int. Ed. 2016, 55, 6075.
[41]
Gong, J.; Wan, Q.; Kang, Q. Adv. Synth. Catal. 2018, 360, 4031.
[42]
(a) Yang, W.-L.; Shang, X.-Y.; Luo, X.; Deng, W.-P. Angew. Chem., Int. Ed. 2022, 61, e202203661.
[42]
(b) Yuen, D.-Y.; Yang, S.-H.; Brimble, M. A. Angew. Chem., nt. Ed. 2011, 50, 8350.
[43]
Yang, W.-L.; Wang, Y.-L.; Li, W.; Gu, B.-M.; Wang, S.-W.; Luo, X.; Tian, B.-X.; Deng, W.-P. ACS Catal. 2021, 11, 12557.
[44]
Chen, J.-R.; Hu, X.-Q.; Xiao, W.-J. Angew. Chem., Int. Ed. 2014, 53, 4038.
[45]
(a) Wang, D.; Liu, S.; Lan, X.-C.; Paniagua, A.; Hao, W.-J.; Li, G.; Tu, S.-J.; Jiang, B. Adv. Synth. Catal. 2017, 359, 3186.
[45]
(b) Liu, S.; Chen, K.; Lan, X.-C.; Hao, W.-J.; Li, G.; Tu, S.-J.; Jiang, B. Chem. Commun. 2017, 53, 10692.
[45]
(c) Liu, S.; Lan, X.-C.; Chen, K.; Hao, W.-J.; Li, G.; Tu, S.-J.; Jiang, B. Org. Lett. 2017, 19, 3831.
[45]
(d) Qiu, J.-K.; Hao, W.-J.; Li, G.; Jiang, B. Adv. Synth. Catal. 2018, 360, 1182.
[45]
(e) Ji, C.-L.; Pan, Y.; Geng, F.-Z.; Hao, W.-J.; Tu, S.-J.; Jiang, B. Org. Chem. Front. 2019, 6, 474.
[46]
Ge, S.; Cao, W.; Kang, T.; Hu, B.; Zhang, H.; Su, Z.; Liu, X.; Feng, X. Angew. Chem., Int. Ed. 2019, 58, 4017.
[47]
Dong, K.; Gurung, R.; Xu, X.; Doyle, M. P. Org. Lett. 2021, 23, 3955.
文章导航

/

〈 〉