A Diastereoselective Route to Benzoannelated Bridged Sultams

Anastasiia A. Klochkova; Valentin A. Rassadin; Victor V. Sokolov

doi:10.1055/a-1531-2176

Synthesis, Table of Contents

Synthesis 2021; 53(23): 4484-4494
DOI: 10.1055/a-1531-2176

paper

A Diastereoselective Route to Benzoannelated Bridged Sultams

Authors

Anastasiia A. Klochkova
Valentin A. Rassadin
Victor V. Sokolov∗

Abstract

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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

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References

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
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

Supplementary Material

Supporting Information (PDF)