A Diastereoselective Route to Benzoannelated Bridged Sultams

Abstract

A practical diastereoselective method for the synthesis of benzoannelated tri- and tetracyclic bridged sultams has been developed. The synthetic route employs widely available, substituted o-iodoanilines and is based on intramolecular Michael addition followed by cycloalkylation with α,ω-dihaloalkanes, or vice versa. The target compounds were isolated in good yields and the diastereoselectivity of the reaction could be easily controlled by the order of Michael addition and cycloalkylation steps.

Key words

heterocycles - bridged sultams - Michael addition - cycloalkylation - diastereoselective synthesis

Publication History

Received: 12 May 2021

Accepted after revision: 17 June 2021

Accepted Manuscript online:
17 June 2021

Article published online:
04 August 2021

• References

• 1 Xu S, Rouzer CA, Marnett LJ. IUBMB Life 2014; 66: 803
• 2 Zia-ur-Rehman M, Choudary JA, Ahmad S, Siddiqui HL. Chem. Pharm. Bull. 2006; 54: 1175
• 3 Zhuang L, Wai JS, Embrey MW, Fisher TE, Egbertson MS, Payne LS, Guare JP. Jr, Vacca JP, Hazuda DJ, Felock PJ, Wolfe AL, Stillmock KA, Witmer MV, Moyer G, Schleif WA, Gabryelski LJ, Leonard YM, Lynch JJ. Jr, Michelson SR, Young SD. J. Med. Chem. 2003; 46: 453
• 4 Valente C, Guedes RC, Moreira R, Iley J, Gut J, Rosenthal PJ. Bioorg. Med. Chem. Lett. 2006; 16: 4115
• 5 Zhang L, Zhu L, Yang J, Luo J, Hong R. J. Org. Chem. 2016; 81: 3890
• 6 Reiser O. In Organic Synthesis Highlights IV . Schmalz H.-G. Wiley-VCH; Weinheim: 2000: 11
• 7 Oppolzer W. Pure Appl. Chem. 1990; 62: 1241
• 8 Oppolzer W, Chauis C, Bernardinelli G. Helv. Chim. Acta 1984; 67: 1397
• 9 Lee AW. M, Chan WH, Zhang S.-J, Zhang H.-K. Curr. Org. Chem. 2007; 11: 213
• 10 Kim BH, Curran DP. Tetrahedron 1993; 49: 293
• 11 Grygorenko OO, Vashchenko BV, Blahun OP, Zhersh S. Eur. J. Org. Chem. 2020; 5787
• 12 Majumdar KC, Mondal S. Chem. Rev. 2011; 111: 7749
• 13 Szostak M, Aube J. Chem. Rev. 2013; 113: 5701
• 14 Debnath S, Mondal S. Eur. J. Org. Chem. 2018; 933
• 15 Rassadin VA, Grosheva DS, Tomashevskiy AA, Sokolov VV. Chem. Heterocycl. Compd. 2013; 49: 39
• 16 Geoghegan K, Evans P, Rozas I, Alkorta I. Chem. Eur. J. 2012; 18: 13379
• 17 Evans P, Grigg R, York M. Tetrahedron Lett. 2000; 41: 7255
• 18 Paquette LA, Barton WR. S, Gallucci JC. Org. Lett. 2004; 6: 1313
• 19 Paquette LA, Sup Ra C, Schloss JD, Leit SM, Gallucci JC. J. Org. Chem. 2001; 66: 3564
• 20 Preston AJ, Gallucci JC, Paquette LA. J. Org. Chem. 2006; 71: 6573
• 21 Dyachenko MS, Dobrydnev AV, Chuchvera YO, Shishkina SV, Volovenko YM. Chem. Heterocycl. Comp. 2020; 56: 386
• 22 Dibchak D, Shcherbacova V, Denisenko AV, Mykhailiuk PK. Org. Lett. 2019; 21: 8909
• 23 Samarakoon TB, Loh JK, Rolfe A, Le LS, Yoon Y, Lushington GH, Hanson PR. Org. Lett. 2011; 13: 5148
• 24 Borgohain H, Devi R, Dheer D, Borah BJ, Shankar R, Das SK. Eur. J. Org. Chem. 2017; 6671
• 25 Qian L, Min X, Hu Y, Shen B, Yang S, Wan B, Chen Q. Chem. Commun. 2020; 56: 2614
• 26 Stepannikova KO, Vashchenko BV, Grygorenko OO, Gorichko MV, Cherepakha AYu, Moroz YS, Volovenko YM, Zhersh S. Eur. J. Org. Chem. 2020; in press DOI: 10.1002/ejoc.202000351.
• 27 Stoll AH, Blakey SB. Chem. Sci. 2011; 2: 112
• 28 Stoll AH, Blakey SB. J. Am. Chem. Soc. 2010; 132: 2108
• 29 Mulet C, Escolano M, Llopis S, Sanz S, de Arellano CR, Sánchez-Roselló M, Fustero S, del Pozo C. Adv. Synth. Catal. 2018; 360: 2885
• 30 Bertuzzi G, Silvestrini F, Moimare P, Pecorari D, Mazzanti A, Bernardi L, Fochia M. Adv. Synth. Catal. 2020; 362: 1
• 31 Grosheva DS, Rassadin VA, Sokolov VV. Eur. J. Org. Chem. 2015; 1355
• 32 Rassadin VA, Grosheva DS, Tomashevskiy AA, Yufit DS, Kozhushkov SI, Sokolov VV, de Meijere A. Eur. J. Org. Chem. 2010; 3481
• 33 Davies SG, Mujtaba N, Roberts PM, Smith AD, Thomson JE. Org. Lett. 2009; 11: 1959
• 34 Harrison JG, Gutierrez O, Jana N, Driver TG, Tantillo DJ. J. Am. Chem. Soc. 2016; 138: 487
• 35 Rassadin VA, Grosheva DS, Arefeva IA, Tomashevskiy AA, Sokolov VV, de Meijere A. Eur. J. Org. Chem. 2012; 5028
• 36 Rassadin VA, Tomashevskii AA, Sokolov VV, Potekhin AA. Chem. Heterocycl. Compd. 2008; 44: 474
• 37 Sheldrick GM. Acta Crystallogr., Sect. A 2008; 64: 112
• 38 Dolomanov OV, Bourhis LJ, Gildea RJ, Howard JA. K, Puschmann H. J. Appl. Crystallogr. 2009; 42: 339
• 39 CrysAlis^Pro Version 1.171.36.20. Agilent Technologies; 2012
• 40 CCDC 1897706 (endo-10a), CCDC 1897703 (endo-12a), CCDC 1897705 (exo-12a), CCDC 1897704 (endo-14), CCDC 1897708 (exo-14), and CCDC 1897707 (endo-18a) contain the supplementary crystallographic data for this paper. The data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/getstructures