Decarboxylative, Diastereoselective and exo-Selective 1,3-Dipolar Cycloaddition for Diversity-Oriented Construction of Structural Spiro[Butyrolactone–Pyrrolidine–Chromanone] Hybrids

Dong-Gui Guo; Zheng Li; Xiao-Xue Han; Lei Zhang; Min Zhang; Xiong-Li Liu

doi:10.1055/a-1535-8891

Synlett, Table of Contents

Synlett 2021; 32(14): 1447-1452
DOI: 10.1055/a-1535-8891

letter

Decarboxylative, Diastereoselective and exo-Selective 1,3-Dipolar Cycloaddition for Diversity-Oriented Construction of Structural Spiro[Butyrolactone–Pyrrolidine–Chromanone] Hybrids

Authors

Dong-Gui Guo

^aCollege of Food and Pharmaceutical Engineering, Guizhou Institute of Technology, Guiyang, 550025, P. R. of China
Zheng Li

^bNational & Local Joint Engineering Research Center for the Exploitation of Homology Resources of Medicine and Food, Guizhou University, Guiyang, Guizhou 550025, P. R. of China
Xiao-Xue Han

^bNational & Local Joint Engineering Research Center for the Exploitation of Homology Resources of Medicine and Food, Guizhou University, Guiyang, Guizhou 550025, P. R. of China
Lei Zhang

^bNational & Local Joint Engineering Research Center for the Exploitation of Homology Resources of Medicine and Food, Guizhou University, Guiyang, Guizhou 550025, P. R. of China
Min Zhang

^bNational & Local Joint Engineering Research Center for the Exploitation of Homology Resources of Medicine and Food, Guizhou University, Guiyang, Guizhou 550025, P. R. of China
Xiong-Li Liu ∗

^bNational & Local Joint Engineering Research Center for the Exploitation of Homology Resources of Medicine and Food, Guizhou University, Guiyang, Guizhou 550025, P. R. of China

Abstract

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Abstract

Inspired by the chemistry and biology of butyrolactones, pyrrolidines, and chromanones, we successfully developed a simple domino 1,3-dipolar cycloaddition of homoserine-lactone-derived azomethine ylides for the construction of biologically important spiro[butyrolactone–pyrrolidine–chromanone] hybrids in the presence of Et₃N as a catalyst under mild conditions. The reaction is based on the application of carboxylic-acid-activated chromones as dienophiles, followed by a decarboxylation process. This reaction displayed good substrate tolerance and gave the desired products in moderate to good yields with high diastereoselectivities (up to 85% yield and >20:1 diastereomeric ratio) via an exo-transition state. This is the first example of an introduction of a chromanone moiety into a spiro[butyrolactone-pyrrolidine] framework, which might be valuable in medicinal chemistry.

Key words

1,3-dipolar cycloaddition - chromones - spiro compounds - azomethine ylides - pyrrolidines - lactones

Full Text

References

References and Notes

1a Nicolaou KC, Vourloumis D, Winssinger N, Baran PS. Angew. Chem. Int. Ed. 2000; 39: 44
1b Wetzel S, Bon RS, Kumar K, Waldmann H. Angew. Chem. Int. Ed. 2011; 50: 10800
1c Zhang Y.-C, Jiang F, Shi F. Acc. Chem. Res. 2020; 53: 425
1d Cao Z.-Y, Zhou F, Zhou J. Acc. Chem. Res. 2018; 51: 1443
1e Miao H.-J, Wang L.-L, Han H.-B, Zhao Y.-D, Wang Q.-L, Bu Z.-W. Chem. Sci. 2020; 11: 1418
1f Han B, He X.-H, Liu Y.-Q, He G, Peng C, Li J.-L. Chem. Soc. Rev. 2021; 50: 1522
1g Bai X.-G, Miao H.-J, Zhao Y, Wang Q.-L, Bu Z.-W. Org. Lett. 2020; 22: 5068

2a Schreiber SL. Science 2000; 287: 1964
2b Chen C, Li X, Schreiber SL. J. Am. Chem. Soc. 2003; 125: 10174

3a Kesava-Reddy N, Golz C, Strohmann C, Kumar K. Chem. Eur. J. 2016; 22: 18373
3b Raksat A, Maneerat W, Rujanapun N, Andersen RJ, Pyne SG, Laphookhieo S. J. Nat. Prod. 2019; 82: 2343
3c Do TM. L, Truong AV, Pinnock TG, Pratt LM, Yamamoto S, Watarai H, Nguyen KP. P. Chem. Pharm. Bull. 2013; 61: 624
3d Li W, Li S, Higai K, Sasaki T, Asada Y, Ohshima S, Koike K. Bioorg. Med. Chem. Lett. 2013; 23: 5836
3e Li W, Asada Y, Yoshikawa T. Phytochemistry 2000; 55: 447
3f Zhao C, Shah BH, Li H, Wu X, Zhang YJ. Asian J. Org. Chem. 2021; 10: 545

4a Hong L, Wang R. Adv. Synth. Catal. 2013; 355: 1023
4b Galliford CV, Scheidt KA. Angew. Chem. Int. Ed. 2007; 46: 8748
4c Kang T.-H, Matsumoto K, Murakami Y, Takayama H, Kitajima M, Aimi N, Watanabe H. Eur. J. Pharmacol. 2002; 444: 39
4d Lee KK, Zhou BN, Kingston DG. I, Vaisberg AJ, Hammond GB. Planta Med. 1999; 65: 759
4e Raj AA, Raghunathan R, SrideviKumari MR, Raman N. Bioorg. Med. Chem. 2003; 11: 407
4f Li Q.-H, Liu T.-L, Wei L, Zhou X, Tao H.-Y, Wang C.-J. Chem. Commun. 2013; 49: 9642
4g Teng H.-L, Huang H, Wang C.-J. Chem. Eur. J. 2012; 18: 12614
4h Wu Y, Liu H, Zhang L, Sun Z, Xiao Y, Huang J, Wang M, Guo H. RSC Adv. 2016; 6: 73547
4i Zhong Y, Hong S, Cai Z, Ma S, Jiang X. RSC Adv. 2018; 8: 28874

5a Sun M.-r, Lu H.-t, Wang Y.-z, Yang H, Liu H.-m. J. Org. Chem. 2009; 74: 2213
5b Becker MH, Chua P, Downham R, Douglas CJ, Garg NK, Hiebert S, Jaroch S, Matsuoka RT, Middleton JA, Ng FW, Overman LE. J. Am. Chem. Soc. 2007; 129: 11987 ; corrigendum: J. Am. Chem. Soc. 2018, 140, 5319

6 Hazra A, Bharitkar YP, Chakraborty D, Mondal SK, Singal N, Mondal S, Maity A, Paira R, Banerjee S, Mondal NB. ACS Comb. Sci. 2013; 15: 41

7a Longmire JM, Wang B, Zhang X. J. Am. Chem. Soc. 2002; 124: 13400
7b Gothelf AS, Gothelf KV, Hazell RG, Jørgensen KA. Angew. Chem. Int. Ed. 2002; 41: 4236
7c Pellissier H. Tetrahedron 2012; 68: 2197
7d Adrio J, Carretero JC. Chem. Commun. 2011; 47: 6784
7e Stanley LM, Sibi MP. Chem. Rev. 2008; 108: 2887

8a Grigg R, Kilner C, Sarker MA. B, Orgaz de la Cierva C, Dondas HA. Tetrahedron 2008; 64: 8974
8b Grigg R, Sarker MA. B. Tetrahedron 2006; 62: 10332
8c Wang L, Shi XM, Dong WP, Zhua LP, Wang R. Chem. Commun. 2013; 49: 3458
8d Tang L.-W, Li C, Zhao B.-J, Lan L, Zhang M, Zhou Z.-M. Tetrahedron 2017; 73: 923
8e Liu T.-L, He Z.-L, Tao H.-Y, Wang C.-J. Chem. Eur. J. 2012; 18: 8042
8f Liu H.-C, Tao H.-Y, Cong H, Wang C.-J. J. Org. Chem. 2016; 81: 3752
8g Liu K, Xiong Y, Wang Z.-F, Tao H.-Y, Wang C.-J. Chem. Commun. 2016; 52: 9458
8h Cayuelas A, Ortiz R, Nájera C, Sansano JM, Larrañaga O, de Cózar A, Cossío FP. Org. Lett. 2016; 18: 2926
8i Kowalczyk-Dworak D, Albrecht Ł. Org. Biomol. Chem. 2019; 17: 2624
8j Chen N, Zhu L, Gan L, Liu Z, Wang R, Cai X, Jiang X. Eur. J. Org. Chem. 2018; 2939
8k Fang X, Dong X.-Q, Wang C.-J. Tetrahedron Lett. 2014; 55: 5660
8l García-Mingüens E, Caletková O, Berkeš D, Nájera C, Sansano JM. Eur. J. Org. Chem. 2020; 5563

9a Viegas-Junior C, Danuello A, Bolzani VD. S, Barreiro EJ, Fraga CA. M. Curr. Med. Chem. 2007; 14: 1829
9b Li JW.-H, Vederas JC. Science 2009; 325: 161
9c Kumar K, Waldmann H. Angew. Chem. Int. Ed. 2009; 48: 3224
9d Koch MA, Schuffenhauer A, Scheck M, Wetzel S, Casaulta M, Odermatt A, Ertl P, Waldmann H. Proc. Natl. Acad. Sci. U.S.A. 2005; 102: 17272
9e Jin S, Wang L, Han H, Liu X, Bu Z, Wang Q. Chem. Commun. 2021; 57: 359
9f Zhang K, Han H, Wang L, Zhang Z, Wang Q, Bu Z. Chem. Commun. 2019; 55: 13681
9g Sheng F.-T, Wang J.-Y, Tan W, Zhang Y.-C, Shi F. Org. Chem. Front. 2020; 7: 3967

10a Liu X.-L, Zhou G, Gong Y, Yao Z, Zuo X, Zhang W.-H, Zhou Y. Org. Lett. 2019; 21: 2528
10b Liu X.-L, Gong Y, Chen S, Zuo X, Yao Z, Zhou Y. Org. Chem. Front. 2019; 6: 1603
10c Liu X.-L, Zuo X, Wang J.-X, Chang S.-q, Wei Q.-D, Zhou Y. Org. Chem. Front. 2019; 6: 1485
10d Zuo X, Liu X.-L, Wang J.-X, Yao Y.-M, Zhou Y.-Y, Wei Q.-D, Gong Y, Zhou Y. J. Org. Chem. 2019; 84: 6679
10e Liu X.-L, Wei Q.-D, Zuo X, Xu S.-W, Yao Z, Wang J.-X, Zhou Y. Adv. Synth. Catal. 2019; 361: 2836
10f Zhang M, Gong Y, Zhou W, Zhou Y, Liu X.-L. Org. Chem. Front. 2021;

11a Amantini D, Fringuelli F, Piermatti O, Pizzo F, Vaccaro L. J. Org. Chem. 2003; 68: 9263
11b Girotti R, Marrocchi A, Minuti L, Piermatti O, Pizzo F, Vaccaro L. J. Org. Chem. 2006; 71: 70
11c Jung ME, Allen DA. Org. Lett. 2009; 11: 757
11d Ballerini E, Minuti L, Piermatti O, Pizzo F. J. Org. Chem. 2009; 74: 4311
11e Albrecht A, Bojanowski J, Kot A, Sieroń L. Org. Biomol. Chem. 2019; 17: 4238
11f Zuo X, Chen S, Xu S.-W, Chang S.-Q, Liu X.-L, Zhou Y, Yuan W.-C. Synthesis 2019; 51: 2339
11g Che C, Li S, Jiang X, Quan J, Lin S, Yang Z. Org. Lett. 2010; 12: 4682
11h Yue J, Chen S, Zuo X, Liu X.-L, Xu S.-W, Zhou Y. Tetrahedron Lett. 2019; 60: 137
11i Liu X.-W, Yue J, Li Z, Wu D, Tian M.-Y, Wang Q.-L, Zhou Y. Tetrahedron 2020; 76: 131678
11j Liu X.-W, Chang S.-Q, Wang Q.-L, Chen S, Wang J.-X, Zhou W, Zhou Y. Synthesis 2020; 52: 3018
11k Zhou F, Zhu L, Pan B.-W, Shi Y, Liu Y.-L, Zhou J. Chem. Sci. 2020; 11: 9341

12 7-Methyl-1-phenyl-1,4′,5′,9a-tetrahydro-3aH-spiro[chromeno[2,3-c]pyrrole-3,3′-furan]-2′,9(2H)-dione (3b); Typical Procedure Compound 1a (0.30 mmol) and compound 2b (0.20 mmol) were dissolved in CH₂Cl₂ (1.5 mL). Et₃N (1.3 equiv, 0.26 mmol) was added to this solution at rt, and the mixture was stirred for 48 h. After the removal of the solvent, purification by flash column chromatography [silica gel, hexane–EtOAc (5:1)] gave a light-yellow solid; yield: 49.6 mg (71%; 16:1 dr); mp 216.3–216.9 °C. ¹H NMR (400 MHz, CDCl₃): δ = 2.23 (s, 3 H), 2.29–2.34 (m, 1 H), 2.44–2.52 (m, 1 H), 2.99–3.02 (m, 1 H), 4.26–4.33 (m, 1 H), 4.36–4.41 (m, 1 H), 4.91–4.96 (m, 2 H), 6.82 (d, J = 8.8 Hz, 1 H), 7.19–7.32 (m, 6 H), 7.57 (s, 1 H). ¹³C NMR (100 MHz, CDCl₃): δ = 19.4, 36.0, 55.0, 62.5, 63.9, 68.7, 83.5, 116.9, 117.8, 125.4, 125.8, 126.9, 127.5, 130.8, 136.7, 140.1, 155.9, 174.5, 188.3. HRMS (ESI-TOF): m/z [M + Na]⁺ calcd for C₂₁H₁₉NNaO₄: 372.1206; found: 372.1207.
13 CCDC 2074189 and 2074188 contain the supplementary crystallographic data for compounds 3b and 3t, respectively. The data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/structures.

14a Pandey G, Banerjee P, Gadre SR. Chem. Rev. 2006; 106: 4484
14b Kim H.-Y, Li J.-Y, Kim S, Oh K. J. Am. Chem. Soc. 2011; 133: 20750 ; corrigendum: J. Am. Chem. Soc. 2012, 134, 16918
14c Arai T, Yokoyama N, Mishiro A, Sato H. Angew. Chem. 2010; 122: 8067 ; Angew. Chem. Int. Ed. 2010, 49, 7895

15 Zhang Y, Chen S, Wei C, Pankin GO, Ye X, Chen YC. Eur. J. Med. Chem. 2018; 147: 218

Supplementary Material

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