中环大环化合物合成研究进展

doi:10.6023/cjoc202010026

摘要/Abstract

中环(8~11元环)与大环(12元环及以上)是药物和天然产物中非常重要的结构并广泛应用于药物合成、有机化学以及其他领域. 科研工作者一直致力于开发更加简单、绿色、高效的合成中环大环的方法. 归纳并总结近五年来最新的通过扩环和环化反应方法合成中环大环化合物的研究现状和进展, 并对其未来的发展方向进行了总结和展望.

关键词: 中环化合物, 大环化合物, 扩环反应, 环化反应

Medium-sized rings (8~11 membered ring) and macrocycles (12-membered rings and above) are extremely important parts of drug and natural products. Meanwhile, they are widely used in the field of medicinal chemistry, organic chemistry and other fields. Developing simple, green and efficient protocol to synthesize medium-sized rings and macrocycles has attracted great interests from chemists in the recent years. The latest ring expansion/cyclization reaction in the synthesis of medium-sized ring and macrocyclic compounds in the past five years is reviewed, and the prospect of their future and development is also outlined.

Key words: medium-sized ring, macrocycle, ring expansion reaction, cyclization

引用此文

张馨元, 林礼, 李静, 段世妤, 隆宇航, 李加洪. 中环大环化合物合成研究进展[J]. 有机化学, 2021, 41(5): 1878-1887.

Xinyuan Zhang, Li Lin, Jing Li, Shiyu Duan, Yuhang Long, Jiahong Li. Recent Progress in the Synthesis of Medium-Sized Ring and Macrocyclic Compounds[J]. Chinese Journal of Organic Chemistry, 2021, 41(5): 1878-1887.

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图/表 28

图式1. 大环二肽的合成策略

Scheme 1. Synthesis strategy toward macrocyclic depsipeptides

图式2. Ugi多组分反应

Scheme 2. Ugi multicomponent reaction

图式3. 氢烷氧化/[1,3]-重排反应

Scheme 3. Hydroalkoxylation/stereospecific [1,3]-rearrangement

图式4. 环化/扩环级联反应

Scheme 4. Cyclisation/ring expansion cascade synthesis

图式5. Double Nicholas反应

Scheme 5. Double Nicholas reaction

图式6. AuI催化1-烯-4,10-二炔酯的反应

Scheme 6. AuI-catalyzed reactivities of 1-ene-4,10-diynyl esters

图式7. 环状β-酮酸酯SuRE反应

Scheme 7. SuRE reaction of cyclic β-ketoester

图式8. SuRE反应

Scheme 8. Successive ring-expansion (SuRE)

图式9. 内酰胺SuRE反应

Scheme 9. SuRE reaction of lactam

图式10. 大环内酯SuRE反应

Scheme 10. SuRE reaction of macrolide

图式11. Smiles重排扩环反应

Scheme 11. Smiles rearrangement ring expansion reaction

图式12. 环状半缩醛的催化扩环反应

Scheme 12. Catalytic ring expansion of cyclic hemiaminals

图式13. Michael加成/扩环级联反应

Scheme 13. Michael addition and ring expansion cascade

图式14. 钌(0)催化二醇二烯[4+2]环加成

Scheme 14. Ruthenium(0) catalyzed diol-diene [4+2] cycloaddition

图式15. [5+4]环加成反应

Scheme 15. [5+4] Cycloaddition

图式16. 胺与硫醇双活化催化的[5+3]环加成反应

Scheme 16. [5+3] Cycloaddition catalyzed by double activation of amine and mercaptan

图式17. 逐步氧化去芳构化扩环反应

Scheme 17. Stepwise oxidative dearomatization-ring-expanding rearomatization

图式18. ODRE反应

Scheme 18. ODRE reaction

图式19. n+3扩环反应

Scheme 19. n+3 Ring expansion

图式20. 烯烃的1,2-甲酰基官能化及其合成应用

Scheme 20. 1,2-Formylfunctionalization of alkenes and synthetic applications

图式21. 1,4-或1,5-芳基迁移/扩环反应

Scheme 21. 1,4- or 1,5-Aryl migration/ring expansion

图式22. 远程乙烯基迁移和合成应用

Scheme 22. Remote radical vinyl migration and synthetic application

图式23. 远程乙烯基迁移机理

Scheme 23. Proposed mechanism for remote radical vinyl migration

图式24. Beckwith-Dowd扩环级联反应

Scheme 24. Cascade Beckwith-Dowd ring expansion/ cyclization

图式25. Beckwith-Dowd扩环

Scheme 25. Beckwith-Dowd ring expansion

图式26. 酮合成中型内酰胺的扩环反应

Scheme 26. Ring-expansion strategies for synthesis of medium-sized lactams from ketones

图式27. 质子偶合电子转移导致的扩环反应

Scheme 27. PCET-enabled ring-expansion

图式28. 通过C—C裂解电化学合成内酰胺

Scheme 28. Electrochemical synthesis of lactams by C—C cleavage

参考文献 39

[1]	Hesse, M. Ring Enlargement in Organic Chemistry, Wiley-VCH, Weinheim, Germany, 1991.
[2]	(a) Clarke, A. K.; Unsworth, W. P. Chem. Sci. 2020, 11, 2876. doi: 10.1039/D0SC00568A
	(b) Terrett, N. K. Drug Discovery Today: Technol. 2010, 7, e97. doi: 10.1016/j.ddtec.2010.06.002
	(c) Hussain, A.; Yousuf, S. K.; Mukherjee, D. RSC Adv. 2014, 4, 43241. doi: 10.1039/C4RA07434C
[3]	Khan, A. R.; Parrish, J. C.; Fraser, M. E.; Smith, W. W.; Bartlett, P. A.; James, M. N. G. Biochemistry 1998, 37, 16839. doi: 10.1021/bi9821364
[4]	Kwon, Y.-U.; Kodadek, T. Cell Chem. Biol. 2007, 14, 671.
[5]	Maier, M. E. Angew. Chem., nt. Ed. 2000, 39, 2073.
[6]	Zhao, Y.; Lv, Y.; Xia, W. Chem. Rec. 2018, 19, 424. doi: 10.1002/tcr.v19.2-3
[7]	Yet, L. Chem. Rev. 2000, 100, 2963. doi: 10.1021/cr990407q
[8]	Vougioukalakis, G. C.; Grubbs, R. H. Chem. Rev. 2010, 110, 1746. doi: 10.1021/cr9002424
[9]	(a) Beck, B.; Larbig, G.; Mejat, B.; Magnin-Lachaux, M.; Picard, A.; Herdtweck, E.; Dömling, A. Org. Lett. 2003, 5, 1047. doi: 10.1021/ol034077e
	(b) Leon, F.; Rivera, D. G.; Wessjohann, L. A. J. Org. Chem. 2008, 73, 1762. doi: 10.1021/jo7022125
	(c) Abdelraheem, E. M. M.; Kurpiewska, K.; Kalinowska-Tłuścik, J.; Dömling, A. J. Org. Chem. 2016, 81, 8789. doi: 10.1021/acs.joc.6b01430
[10]	Abdelraheem, E. M. M.; Madhavachary, R.; Rossetti, A.; Kurpiewska, K.; Kalinowska-Tłuścik, J.; Shaabani, S.; Dömling, A. Org. Lett. 2017, 19, 6176. doi: 10.1021/acs.orglett.7b03094
[11]	Madhavachary, R.; Abdelraheem, E. M. M.; Rossetti, A.; Twarda- Clapa, A.; Musielak, B.; Kurpiewska, K.; Kalinowska-Tłuścik, J.; Holak, T. A.; Dömling, A. Angew. Chem., nt. Ed. 2017, 56, 10725.
[12]	Zhou, B.; Zhang, Y.-Q.; Zhang, K.; Yang, M.-Y.; Chen, Y.-B.; Li, Y.; Peng, Q.; Zhu, S.-F.; Zhou, Q.-L.; Ye, L.-W. Nat. Commun. 2019, 10, 3234. doi: 10.1038/s41467-019-11245-2 pmid: 31324800
[13]	Lawer, A.; Rossi-Ashton, J. A.; Stephens, T. C.; Challis, B. J.; Epton, R. G.; Lynam, J. M.; Unsworth, W. P. Angew. Chem.,Int. Ed. 2019, 58, 13942. doi: 10.1002/anie.v58.39
[14]	Ni, R.; Mitsuda, N.; Kashiwagi, T.; Igawa, K.; Tomooka, K. Angew. Chem., nt. Ed. 2015, 54, 1190.
[15]	Mathiew, M.; Tan, J. K.; Chan, P. W. H. Angew. Chem., nt. Ed. 2018, 57, 14235.
[16]	Kitsiou, C.; Hindes, J. J.; I'Anson, P.; Jackson, P.; Wilson, T. C.; Daly, E. K.; Felstead, H. R.; Hearnshaw, P.; Unsworth, W. P. Angew. Chem., nt. Ed. 2015, 54, 15794.
[17]	Stephens, T. C.; Lodi, M.; Steer, A. M.; Lin, Y.; Gill, M. T.; Unsworth, W. P. Chem.-Eur. J. 2017, 23, 13314.
[18]	Stephens, T. C.; Lawer, A.; French, T.; Unsworth, W. P. Chem.-Eur. J. 2018, 24, 13947. doi: 10.1002/chem.201803064
[19]	Costil, R.; Lefebvre, Q.; Clayden, J. Angew. Chem., nt. Ed. 2017, 56, 14602.
[20]	Zhao, W.; Qian, H.; Li, Z.; Sun, J. Angew. Chem., nt. Ed. 2015, 54, 10005.
[21]	Zhou, Y.; Wei, Y. L.; Rodriguez, J.; Coquerel, Y. Angew. Chem., nt. Ed. 2019, 58, 456.
[22]	Kasun, Z. A.; Geary, L. M.; Krische, M. J. Chem. Commun. 2014, 50, 7545. doi: 10.1039/c4cc03983a
[23]	Yang, L. C.; Rong, Z. Q.; Wang, Y. N.; Tan, Z. Y.; Wang, M.; Zhao, Y. Angew. Chem., nt. Ed. 2017, 56, 2927.
[24]	Wang, Y. N.; Yang, L. C.; Rong, Z. Q.; Liu, T. L.; Liu, R.; Zhao, Y. Angew. Chem., nt. Ed. 2018, 57, 1596.
[25]	Yang, Q.-Q.; Yin, X.; He, X.-L.; Du, W.; Chen, Y.-C. ACS Catal. 2019, 9, 1258. doi: 10.1021/acscatal.8b04942
[26]	Bauer, R. A.; Wenderski, T. A.; Tan, D. S. Nat. Chem. Biol. 2013, 9, 21. doi: 10.1038/NCHEMBIO.1130
[27]	Guney, T.; Wenderski, T. A.; Boudreau, M. W.; Tan, D. S. Chem.- Eur. J. 2018, 24, 13150. doi: 10.1002/chem.201802880
[28]	Hall, J. E.; Matlock, J. V.; Ward, J. W.; Gray, K. V.; Clayden, J. Angew. Chem., nt. Ed. 2016, 55, 11153.
[29]	Li, Z. L.; Li, X. H.; Wang, N.; Yang, N. Y.; Liu, X. Y. Angew. Chem., nt. Ed. 2016, 55, 15100. doi: 10.1002/anie.201608198
[30]	Li, L.; Li, Z.-L.; Wang, F.-L.; Guo, Z.; Cheng, Y.-F.; Wang, N.; Dong, X.-W.; Fang, C.; Liu, J.; Hou, C.; Tan, B.; Liu, X.-Y. Nat. Commun. 2016, 7, 13852. doi: 10.1038/ncomms13852
[31]	Li, L.; Li, Z.-L.; Gu, Q.-S.; Wang, N.; Liu, X.-Y. Sci. Adv. 2017, 3, e1701487. doi: 10.1126/sciadv.1701487
[32]	(a) Dowd, P.; Choi, S. C. J. Am. Chem. Soc. 1987, 109, 3493. doi: 10.1021/ja00245a069
	(b) Beckwith, A. L. J.; O'Shea, D. M.; Westwood, S. W. J. Am. Chem. Soc. 1988, 110, 2565. doi: 10.1021/ja00216a033
[33]	Hierold, J.; Lupton, D. W. Org. Lett. 2012, 14, 3412. doi: 10.1021/ol301386k
[34]	Deguchi, M.; Fujiya, A.; Yamaguchi, E.; Tada, N.; Uno, B.; Itoh, A. RSC Adv. 2018, 8, 15825. doi: 10.1039/C8RA02383B
[35]	Wang, M.; Li, M.; Yang, S.; Xue, X.-S.; Wu, X.; Zhu, C. Nat. Commun. 2020, 11, 672. doi: 10.1038/s41467-020-14435-5
[36]	Wang, N.; Gu, Q.-S.; Li, Z.-L.; Li, Z.; Guo, Y.-L.; Guo, Z.; Liu, X.-Y. Angew. Chem. 2018, 57, 14225. doi: 10.1002/anie.201808890
[37]	Wang, N.; Wang, J.; Guo, Y. L.; Li, L.; Sun, Y.; Li, Z.; Zhang, H. X.; Guo, Z.; Li, Z. L.; Liu, X. Y. Chem. Commun. 2018, 54, 8885. doi: 10.1039/C8CC05186K
[38]	Zhao, K.; Yamashita, K.; Carpenter, J. E.; Sherwood, T. C.; Ewing, W. R.; Cheng, P. T. W.; Knowles, R. R. J. Am. Chem. Soc. 2019, 141, 8752. doi: 10.1021/jacs.9b03973
[39]	Xu, Z.; Huang, Z.; Li, Y.; Kuniyil, R.; Zhang, C.; Ackermann, L.; Ruan, Z. Green Chem. 2020, 22, 1099. doi: 10.1039/C9GC03901E