Recent Progress in the Synthesis of Medium-Sized Ring and Macrocyclic Compounds

doi:10.6023/cjoc202010026

Abstract

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

Cite this article

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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Fig. & Tab. 28

Scheme 1. Synthesis strategy toward macrocyclic depsipeptides

Scheme 2. Ugi multicomponent reaction

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

Scheme 4. Cyclisation/ring expansion cascade synthesis

Scheme 5. Double Nicholas reaction

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

Scheme 7. SuRE reaction of cyclic β-ketoester

Scheme 8. Successive ring-expansion (SuRE)

Scheme 9. SuRE reaction of lactam

Scheme 10. SuRE reaction of macrolide

Scheme 11. Smiles rearrangement ring expansion reaction

Scheme 12. Catalytic ring expansion of cyclic hemiaminals

Scheme 13. Michael addition and ring expansion cascade

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

Scheme 15. [5+4] Cycloaddition

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

Scheme 17. Stepwise oxidative dearomatization-ring-expanding rearomatization

Scheme 18. ODRE reaction

Scheme 19. n+3 Ring expansion

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

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

Scheme 22. Remote radical vinyl migration and synthetic application

Scheme 23. Proposed mechanism for remote radical vinyl migration

Scheme 24. Cascade Beckwith-Dowd ring expansion/ cyclization

Scheme 25. Beckwith-Dowd ring expansion

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

Scheme 27. PCET-enabled ring-expansion

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

References 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

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