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 2014; 46(20): 2794-2798
DOI: 10.1055/s-0034-1378515
DOI: 10.1055/s-0034-1378515
paper
Stereoselective Total Syntheses of Solifenacin and N-Acetyl-1-(4-chlorophenyl)-6,7-dimethoxytetrahydroisoquinoline
Further Information
Publication History
Received: 19 May 2014
Accepted after revision: 24 June 2014
Publication Date:
16 July 2014 (online)
Abstract
A highly stereoselective synthesis of 1-aryl-1,2,3,4-tetrahydroisoquinoline drugs such as solefinacin (muscarinic acetylcholine receptor antagonist) and N-acetyl-1-(4-chlorophenyl)-6,7-dimethoxytetrahydroisoquinoline (AMPA receptor antagonist) has been accomplished using (R)-tert-butanesulfinamide as a chiral source. Chiral tetrahydroisoquinolines have been prepared through the aryl Grignard addition to chiral N-sulfinylimines followed by haloamide cyclization.
Key words
chiral N-sulfinylimine - aryl Grignard reagent - tetrahydroisoquinoline - 3-hydroxyquinuclidineSupporting Information
- for this article is available online at http://www.thieme-connect.com/products/ejournals/journal/ 10.1055/s-00000084.
- Supporting Information
-
References
- 1a Minor DL, Wyrick SD, Charifson PS, Watts VJ, Nichols DE, Mailman RB. J. Med. Chem. 1994; 37: 4317
- 1b Ludwig M, Hoesl CE, Hofner G, Wanner KT. Eur. J. Med. Chem. 2006; 41: 1003
- 1c Gitto R, Ficarra R, Stancanelli R, Guardo M, De Luca L, Barreca ML, Pagano B, Rotondo A, Bruno G, Russo E, De Sarro G, Chimirri A. Bioorg. Med. Chem. 2007; 15: 5417
- 1d Tiwari RK, Singh D, Singh J, Chhillar AK, Chandra R, Verma AK. Eur. J. Med. Chem. 2006; 41: 40
- 1e Chen KX, Xie HY, Li ZG, Gao JR. Bioorg. Med. Chem. Lett. 2008; 18: 5381
- 2 Naito R, Yonetoku Y, Okamoto Y, Toyoshima A, Ikeda K, Takeuchi M. J. Med. Chem. 2005; 48: 6597
- 3 Gitto R, Barreca ML, DeSarro G, Ferreri G, Quartarone S, Russo E, Constanti A, Chimirri A. J. Med. Chem. 2003; 46: 197
- 4 Gao M, Kong D, Clearfield A, Zhenga Q.-H. Bioorg. Med. Chem. Lett. 2006; 16: 2229
- 5a Chang M, Li W, Zhang X. Angew. Chem. Int. Ed. 2011; 50: 10679
- 5b Ishii Y, Takaoka K, Inakoshi M, Nakagawa S, Nagata K, Yorimoto N, Takeuchi M, Yonetoku Y. Patent WO 2005075474A1, 2005
- 5c Bolchi C, Pallavicini M, Fumagalli L, Straniero V, Valoti E. Org. Process Res. Dev. 2013; 17: 432
- 6a Berhal F, Wu Z, Zhang Z, Ayad T, Vidal VR. Org. Lett. 2012; 14: 3308
-
6b Ye Z.-S, Guo RN, Cai X.-F, Chen M.-W, Shi L, Zhou Y.-G. Angew. Chem. Int. Ed. 2013; 52: 3685
- 7a Paul R, Coppola JA, Cohen E. J. Med. Chem. 1972; 15: 720
- 7b The Chemistry and Biology of Isoquinoline Alkaloids . Phillipson JD, Roberts MF, Zenk MH. Springer; Berlin: 1985
- 7c Jack D, Williams R. Chem. Rev. 2002; 102: 1669
- 7d Dewick PM. Medicinal Natural Products: A Biosynthetic Approach. Wiley; Chichester: 2002: 315
- 7e Bentley KW. Nat. Prod. Rep. 2006; 23: 444
- 7f Chrzanowska M, Rozwadowska MD. Chem. Rev. 2004; 104: 3341
- 8a Yamamoto Y, Miyauraa N. Adv. Synth. Catal. 2009; 351: 260
- 8b Umetsu K, Asao N. Tetrahedron Lett. 2008; 49: 2722
- 8c Wang S, Onaran MB, Seto CT. Org. Lett. 2010; 12: 2690
- 8d Louafi F, Hurvois J.-P, Chibani A, Roisnel T. J. Org. Chem. 2010; 75: 5721
- 8e Amat M, Elias V, Llor N, Subrizi F, Molins E, Bosch J. Eur. J. Org. Chem. 2010; 4017
- 9a Ellman JA, Owens TD, Tang TP. Acc. Chem. Res. 2002; 35: 984
- 9b Sun XW, Xu MH, Lin GQ. Org. Lett. 2006; 8: 4979
- 9c Lin GQ, Xu MH, Zhong YW, Sun XW. Acc. Chem. Res. 2008; 41: 831
- 9d Cogan DA, Liu G, Ellman JA. Tetrahedron 1999; 55: 8883
- 10a Robak MT, Herbage MA, Ellman JA. Chem. Rev. 2010; 110: 3600
- 10b Davis FA, Yang B, Deng J, Zhang J. ARKIVOC 2006; (vii): 120
- 10c Bosque I, González-Gómez JC, Foubelo F, Yus M. J. Org. Chem. 2012; 77: 780
- 10d Bosque I, González-Gómez JC, Foubelo F, Yus M. J. Org. Chem. 2012; 77: 4190
- 10e Bosque I, González-Gómez JC, Guijarro A, Foubelo F, Yus M. J. Org. Chem. 2012; 77: 10340
- 10f Davis FA. J. Org. Chem. 2006; 71: 8993
- 10g Zhou P, Chen B-C, Davis FA. Tetrahedron 2004; 60: 8003
- 11a Reddy NS. S, Reddy BJ. M, Reddy BV. S. Tetrahedron Lett. 2013; 54: 4228
- 11b Reddy NS. S, Reddy AS, Yadav JS, Reddy BV. S. Tetrahedron Lett. 2012; 53: 6916
- 11c Reddy NS. S, Reddy BV. S. Tetrahedron Lett. 2014; 55: 3157
- 12a Sakamoto M, Tanaka D, Tsunoyama H, Tsukuda T, Minagawa Y, Majima Y, Teranishi T. J. Am. Chem. Soc. 2012; 134: 816
- 12b Yamato M, Washigaki K, Qais N, Ishikawa S. Tetrahedron 1990; 46: 5909
- 12c Coldham I, Jana S, Watson L, Martin NG. Org. Biomol. Chem. 2009; 7: 1674
- 13a Liu G, Cogan DA, Owens TD, Tang TP, Ellman JA. J. Org. Chem. 1999; 64: 1278
- 13b Harried SS, Croghan MD, Kaller MR, Lopez P, Zhong W, Hungate R, Reider PJ. J. Org. Chem. 2009; 74: 5975
- 14 Plobeck N, Powell D. Tetrahedron: Asymmetry 2002; 13: 303
- 15a Natsume M, Wada M. Chem. Pharm. Bull. 1972; 20: 1589
- 15b Reddy LR, Das SG, Liu Y, Prashad M. J. Org. Chem. 2010; 75: 2236
- 15c Davis FA, Prasad KR, Nolt MB, Wu Y. Org. Lett. 2003; 5: 925
- 15d Davis FA, Rao A, Carroll PJ. Org. Lett. 2003; 5: 3855
- 16a Liu M, Sun X, Xu M, Lin G. Chem. Eur. J. 2009; 15: 10217
- 16b Sun X, Liu M, Xu M, Lin G. Org. Lett. 2008; 10: 1259
-
17a Ye Z.-S, Guo R.-N, Cai X.-F, Chen M.-W, Shi L, Zhou YG. Angew. Chem. Int. Ed. 2013; 52: 3685
- 17b Wu Z, Perez M, Scalone M, Ayad T, Vidal VR. Angew. Chem. Int. Ed. 2013; 52: 4925
- 18a Berhal F, Wu Z, Zhang Z, Ayad T, Vidal VR. Org. Lett. 2012; 13: 3308
- 18b Ghislieri D, Green PA, Simon CP, Rowles WI, Frank A, Grogan G, Turner NJ. J. Am. Chem. Soc. 2013; 135: 10863
- 18c Ryo Naito R, Yonetoku Y, Okamoto Y, Toyoshima A, Ikeda K, Takeuchi M. J. Med. Chem. 2005; 48: 6597
- 18d Bolchi C, Pallavicini M, Fumagalli L, Straniero V, Valoti E. Org. Process Res. Dev. 2013; 17: 432
- 18e Chang M, Li W, Zhang X. Angew. Chem. Int. Ed. 2011; 50: 10679
- 18f García D, Moreno B, Soler T, Foubelo F, Yus M. Tetrahedron Lett. 2009; 50: 4710
- 18g Naito R, Yonetoku Y, Okamoto Y, Toyoshimata A, Ikeda K, Takeuchi MJ. J. Med. Chem. 2005; 48: 6597
- 18h Wang S, Onaran MB, Seto CT. Org. Lett. 2010; 12: 2690