Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Synthesis 2021; 53(16): 2819-2827
DOI: 10.1055/s-0040-1720693
DOI: 10.1055/s-0040-1720693
feature
Alkyl Carbagermatrane Enabled Synthesis of Seven-Membered Carbocycle-Fused Aromatics through Catellani Strategy
We thank the National Natural Science Foundation of China for financial support (21871239, 22022109).
Synthesis of seven-membered carbocycle-fused aromatics was realized by Catellani reaction using terminally brominated alkyl carbagermatranes through intermolecular cyclization manner. Various functional groups were well tolerated, and this transformation was also expanded to the synthesis of carbocycles of other size. The utility of this method was demonstrated by modification of natural product derivatives and synthesis of bioactive molecules.
Key words
Catellani reaction - alkyl carbagermatranes - seven-membered carbocycles - cyclization - organogermaniumSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0040-1720693.
- Supporting Information
Publication History
Received: 03 February 2021
Accepted after revision: 14 April 2021
Article published online:
18 May 2021
© 2021. Thieme. All rights reserved
Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany
-
References
- 1 de Oliveira KT, Servilha BM, Alves L. deC, Desidera AL, Brocksom TJ. Stud. Nat. Prod. Chem. 2014; 42: 421
- 2 Stempel E, Gaich T. Acc. Chem. Res. 2016; 49: 2390
- 3a Murase M, Watanabe K, Yoshida T, Tobinaga S. Chem. Pharm. Bull. 2000; 48: 81
- 3b Su J.-Y, Zhu Y, Zeng L.-M, Xu X.-H. J. Nat. Prod. 1997; 60: 1043
- 3c Liu B.-Y, Zhang C, Zeng K.-W, Li J, Guo X.-Y, Zhao M.-B, Tu P.-F, Jiang Y. Org. Lett. 2015; 17: 4380
- 3d Smitka TA, Bonjouklian R, Doolin L, Jones ND, Deeter JB, Yoshida WY, Prinsep MR, Moore RE, Patterson GM. J. Org. Chem. 1992; 57: 857
- 3e Mo S, Krunic A, Chlipala G, Orjala J. J. Nat. Prod. 2009; 72: 894
- 4a Wang G.-W, Wang H.-L, Capretto DA, Han Q, Hu R.-B, Yang S.-D. Tetrahedron 2012; 68: 5216
- 4b Tanpure RP, George CS, Strecker TE, Devkota L, Tidmore JK, Lin C.-M, Herdman CA, MacDonough MT, Sriram M, Chaplin DJ. Bioorg. Med. Chem. 2013; 21: 8019
- 4c Kramer B, Waldvogel SR. Angew. Chem. Int. Ed. 2004; 43: 2446
- 4d Kita Y, Gyoten M, Ohtsubo M, Tohma H, Takada T. Chem. Commun. 1996; 1481
- 4e Mehdi MA, Djurdjevic S, Green JR. Synlett 2015; 26: 2408
- 5a Lautens M, Piguel S. Angew. Chem. Int. Ed. 2000; 39: 1045
- 5b Lautens M, Paquin J.-F, Piguel S, Dahlmann M. J. Org. Chem. 2001; 66: 8127
- 5c Pache S, Lautens M. Org. Lett. 2003; 5: 4827
- 5d Bressy C, Alberico D, Lautens M. J. Am. Chem. Soc. 2005; 127: 13148
- 5e Kasravi N, Alberico D, Lautens M. J. Org. Chem. 2006; 71: 4937
- 5f Alberico D, Rudolph A, Lautens M. J. Org. Chem. 2007; 72: 775
- 5g Rudolph A, Rackelmann N, Lautens M. Angew. Chem. Int. Ed. 2007; 46: 1485
- 5h Rudolph A, Rackelmann N, Turcotte-Savard M.-O, Lautens M. J. Org. Chem. 2009; 74: 289
- 5i Jafarpour F, Lautens M. Org. Lett. 2006; 8: 3601
- 5j Martins A, Marquardt U, Kasravi N, Alberico D, Lautens M. J. Org. Chem. 2006; 71: 4937
- 5k Liu Z.-S, Qian G, Gao Q, Wang P, Cheng H.-G, Wei Q, Liu Q, Zhou Q. ACS Catal. 2018; 8: 4783
- 5l Wu C, Cheng H.-G, Chen R, Chen H, Liu Z.-S, Zhang J, Zhang Y, Zhu Y, Geng Z, Zhou Q. Org. Chem. Front. 2018; 5: 2533
- 6 Gelis C, Levitre G, Merad J, Retailleau P, Neuville L, Masson G. Angew. Chem. Int. Ed. 2018; 57: 12121
- 7 Matsuda T, Makino M, Murakami M. Angew. Chem. Int. Ed. 2005; 44: 4608
- 8 Tymann D, Tymann DC, Bednarzick U, Iovkova-Berends L, Rehbein J, Hiersemann M. Angew. Chem. Int. Ed. 2018; 57: 15553
- 9 Ydhyam S, Cha JK. Org. Lett. 2015; 17: 5820
- 10 Sperry JB, Wright DL. J. Am. Chem. Soc. 2005; 127: 8034
- 11 Catellani M, Frignani F, Rangoni A. Angew. Chem., Int. Ed. Engl. 1997; 36: 119
- 12a Ye J, Lautens M. Nat. Chem. 2015; 7: 863
- 12b Della Ca’ N, Fontana M, Motti E, Catellani M. Acc. Chem. Rev. 2016; 49: 1389
- 12c Wang J, Dong G. Chem. Rev. 2019; 119: 7478
- 13 Jiang WT, Xu MY, Yang S, Xie XY, Xiao B. Angew. Chem. Int. Ed. 2020; 59: 20450
- 14 Jiang W.-T, Yang S, Xu M.-Y, Xie X.-Y, Xiao B. Chem. Sci. 2020; 11: 488
- 15 Barf T, Lehmann F, Hammer K, Haile S, Axen E, Medina C, Uppenberg J, Svensson S, Rondahl L, Lundbäck T. Bioorg. Med. Chem. Lett. 2009; 19: 1745
- 16 Kong W, Yu C, An H, Song Q. Org. Lett. 2018; 20: 349
- 17 Zhang Y.-L, Yang L, Wu J, Zhu C, Wang P. Org. Lett. 2020; 22: 7768