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A Rh(II)-catalyzed highly stereoselective [3 + 2] annulation of vinyl diazoacetates with indole-2-carbaldehyde for the synthesis of indolyl dihydrofurans

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Abstract

A highly stereoselective Rh2(Oct)4-catalyzed [3 + 2] cycloaddition of vinyl diazoacetates with indolyl aldehyde has been developed. This protocol provides an efficient access to both cis and trans indolyl dihydrofurans with high yields and diastereoselectivities under mild conditions without or with Lewis acid as additive, respectively. Moreover, these generated functionalized dihydrofurans exhibit potent antiproliferation activity in three different cancer cell lines.

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References

  1. De la Torre A, Cuyamendous C, Bultel-Ponce V, Durand T, Galano JM, Oger C (2016) Recent advances in the synthesis of tetrahydrofurans and applications in total synthesis. Tetrahedron 72:5003. https://doi.org/10.1016/j.tet.2016.06.076

    Article  CAS  Google Scholar 

  2. Rainier JD (2014) Synthesis of substituted tetrahydrofurans. Top Heterocycl Chem 35:1. https://doi.org/10.1007/978-3-642-41473-2_1

    Article  CAS  Google Scholar 

  3. Lorente A, Lamariano-Merketegi J, Albericio F, Alvarez M (2013) Tetrahydrofuran-containing macrolides: A fascinating gift from the deep sea. Chem Rev 13:4567. https://doi.org/10.1021/cr3004778

    Article  CAS  Google Scholar 

  4. Nizamuddin GM, Srivastava MK (1999) Synthesis and fungicidal activity of some furan containing azoles. J Sci Ind Res 58:1017

    CAS  Google Scholar 

  5. Kraft P, Bajgrowicz JA, Denis C, Frater G (2000) Odds and trends: recent developments in the chemistry of odorants. Angew Chem Int Ed 39:2981

    Article  Google Scholar 

  6. Anbazhagan M, Boykin DW (2003) A facile synthesis of the prodrug 2,5-bis(4-o-methoxyamidinophenyl)furan and analogs. Heterocycl Commun 9:117. https://doi.org/10.1515/HC.2003.9.2.117

    Article  CAS  Google Scholar 

  7. Castro-Hermida JA, Gomez-Couso H, Ares-Mazas ME, Gonzalez-Edia MM, Castaneda-Cancio N, Otero-Espinar FJ, Blanco-Mendez J (2004) Anticryptosporidial activity of furan derivative g1 and its inclusion complex with beta-cyclodextrin. J Pharm Sci 93:197. https://doi.org/10.1002/jps.10528

    Article  CAS  PubMed  Google Scholar 

  8. Yang P, Yeh T, Loh HH, Law P, Wang Y, Tao P (2019) Delta-opioid receptor antagonist naltrindole reduces oxycodone addiction and constipation in mice. Eur J Pharmacol 852:265. https://doi.org/10.1016/j.ejphar.2019.04.009

    Article  CAS  PubMed  Google Scholar 

  9. Liu Y, Guo Y, Ji F, Gao D, Song C, Chang J (2016) Divergent syntheses of carbazole alkaloids clausenapin, indizoline, claulansine M, and clausenaline D. J Org Chem 81:4310. https://doi.org/10.1021/acs.joc.6b00729

    Article  CAS  PubMed  Google Scholar 

  10. Karadeolian A, Kerr MA (2010) Total synthesis of (+)-isatisine A. Angew Chem Int Ed 49:1133. https://doi.org/10.1002/anie.200906632

    Article  CAS  Google Scholar 

  11. Zhang X, Mu T, Zhan F, Ma L, Liang G (2011) Total synthesis of (−)-isatisine A. Angew Chem Int Ed 50:6164. https://doi.org/10.1002/anie.201101621

    Article  CAS  Google Scholar 

  12. Liu J, Jiang Z, Wang R, Zheng Y, Chen J, Zhang X, Ma Y (2007) Isatisine A, a novel alkaloid with an unprecedented skeleton from leaves of Isatis indigotica. Org Lett 9:4127. https://doi.org/10.1021/ol701540y

    Article  CAS  PubMed  Google Scholar 

  13. Kock M, Fresia M, Jone PG, Lindel T (2019) Synthesis of raputimonoindoles A-C and congeners. Eur J Org Chem 25:4061. https://doi.org/10.1002/ejoc.201900583

    Article  CAS  Google Scholar 

  14. Suga H, Kakehi A, Ito S, Inoue K, Ishida H, Ibata T (2000) Stereocontrol in rare earth metal triflate-catalyzed 1,3-dipolar cycloaddition reaction of 2-benzopyrylium-4-olate with aldehydes. Org Lett 2:3145. https://doi.org/10.1021/ol0063454

    Article  CAS  PubMed  Google Scholar 

  15. Padwa A, Snyder JP, Curtis EA, Sheehan SM, Worsencroft KJ, Kappe CO (2000) Rhodium(II)-catalyzed equilibration of push-pull carbonyl and ammonium ylides. A computationally based understanding of the reaction pathway. J Am Chem Soc 122:8155. https://doi.org/10.1021/ja001088j

    Article  CAS  Google Scholar 

  16. Torssell S, Kienle M, Somfai P (2005) 1,3-Dipolar cycloadditions of carbonyl ylides to aldimines: a three-component approach to syn-α-hydroxy-β-amino esters. Angew Chem Int Ed 44:3096. https://doi.org/10.1002/anie.200500296

    Article  CAS  Google Scholar 

  17. England DB, Eagan JM, Merey G, Anac O, Padwa A (2008) The rhodium(II) carbenoid cyclization–cycloaddition cascade of α-diazo dihydroindolinones for the synthesis of novel azapolycyclic ring systems. Tetrahedron 64:988. https://doi.org/10.1016/j.tet.2007.10.038

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  18. DeAngelis A, Taylor MT, Fox JM (2009) Unusually reactive and selective carbonyl ylides for three-component cycloaddition reactions. J Am Chem Soc 131:1101. https://doi.org/10.1021/ja807184r

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  19. Doyle MP (1995) Transition metal carbene complexes: diazodecomposition, ylide, and insertion. In: Hegedus LS (ed) Comprehensive organometallic chemistry II, vol 12, p 421. Pergamon Press, New York

  20. Padwa A, Weigarten MD (1996) Cascade processes of metallo carbenoids. Chem Rev 96:223. https://doi.org/10.1021/cr950022h

    Article  CAS  PubMed  Google Scholar 

  21. Mehta G, Muthusamy S (2002) Tandem cyclization–cycloaddition reactions of rhodium generated carbenoids from α-diazo carbonyl compounds. Tetrahedron 58:9477. https://doi.org/10.1016/S0040-4020(02)01187-0

    Article  CAS  Google Scholar 

  22. McMills MC, Wright D (2002) Carbonyl ylides. In: Padwa A, Pearson WH (eds) Synthetic applications of 1,3-dipolar cycloaddition chemistry toward heterocycles and natural products, vol 59, p 253. Wiley, New York

  23. Padwa A (2009) Domino reactions of rhodium(ii) carbenoids for alkaloid synthesis. Chem Soc Rev 38:3072. https://doi.org/10.1039/B816701J

    Article  CAS  PubMed  Google Scholar 

  24. Zhao X, Zhang Y, Wang J (2012) Recent developments in copper-catalyzed reactions of diazo compounds. Chem Commun 48:10162. https://doi.org/10.1039/C2CC34406H

    Article  CAS  Google Scholar 

  25. Hamaguchi M, Matsubara H, Nagai T (2000) Reaction of vinylcarbenoids with aldehydes: formation of vinylcarbonyl ylides followed by ring closure to oxiranes and dihydrofurans. Tetrahedron Lett 41:1457. https://doi.org/10.1016/S0040-4039(99)02317-5

    Article  CAS  Google Scholar 

  26. Doyle MP, Hu W, Timmons DJ (2001) Highly stereoselective syntheses of five- and seven-membered ring heterocycles from ylides generated by catalytic reactions of styryldiazoacetates with aldehydes and imines. Org Lett 3:3741. https://doi.org/10.1021/ol016703i

    Article  CAS  PubMed  Google Scholar 

  27. Hamaguchi M, Matsubara H, Nagai T (2001) Reaction of vinylcarbenoids with benzaldehydes: formation of vinylcarbonyl ylides followed by ring closure to oxiranes and dihydrofurans. J Org Chem 66:5395. https://doi.org/10.1021/jo015618l

    Article  CAS  PubMed  Google Scholar 

  28. DeMeese J, Davies HML (2001) Stereoselective synthesis of epoxides by reaction of donor/acceptor-substituted carbenoids with α, β-unsaturated aldehydes. Tetrahedron Lett 42:6803. https://doi.org/10.1016/S0040-4039(01)01415-0

    Article  Google Scholar 

  29. Guo X, Hu W (2013) Novel multicomponent reactions via trapping of protic onium ylides with electrophiles. Acc Chem Res 46:2427. https://doi.org/10.1021/ar300340k

    Article  CAS  PubMed  Google Scholar 

  30. Zhang D, Hu W (2017) Asymmetric multicomponent reactions based on trapping of active intermediates. Chem Rec 17:739. https://doi.org/10.1002/tcr.201600124

    Article  CAS  PubMed  Google Scholar 

  31. Kang Z, Wang Y, Zhang D, Wu R, Xu X, Hu W (2019) Asymmetric counter-anion-directed aminomethylation: synthesis of chiral β-amino acids via trapping of an enol intermediate. J Am Chem Soc 141:1473. https://doi.org/10.1021/jacs.8b12832

    Article  CAS  PubMed  Google Scholar 

  32. Zhang D, Wang X, Zhang M, Kang Z, Xiao G, Xu X, Hu W (2020) Highly enantioselective trapping of carboxylic oxonium ylides with imines for direct assembly of enantioenriched γ-butenolides. CCS Chem 2:432. https://doi.org/10.31635/ccschem.020.201900089

    Article  CAS  Google Scholar 

  33. Zhu D, Xia H, Liu J, Chung L, Xu M (2021) Regiospecific and enantioselective arylvinylcarbene insertion of a C–H bond of aniline derivatives enabled by a Rh(I)-diene catalyst. J Am Chem Soc 143:2608. https://doi.org/10.1021/jacs.0c13191

    Article  CAS  PubMed  Google Scholar 

  34. Zhu D, Liu J, Xu M (2021) Stereodivergent synthesis of enantioenriched 2,3-disubstituted dihydrobenzofurans via a one-pot C-H functionalization/oxa-Michael addition cascade. J Am Chem Soc 143:8583. https://doi.org/10.1021/jacs.1c03498

    Article  CAS  PubMed  Google Scholar 

  35. CCDC 2089997 contains the supplementary crystallographic data for 3h, CCDC 2090004 contains the supplementary crystallographic data for 5g respectively. These data can be obtained free of charge from the Cambridge crystallographic data centre via www.ccdc.cam.ac.uk/data_request/cif

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Acknowledgements

Support for this research from the National Natural Science Foundation of China (22001268, 81973176), Guangdong Provincial Key Laboratory of Chiral Molecule and Drug Discovery (2019B030301005), The Program for Guangdong Introducing Innovative and Entrepreneurial Teams (2016ZT06Y337) and Guangdong Natural Science Fund (2020A1515010614) is greatly acknowledged.

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Author notes

  1. Rimei Zheng and Aimin Xu have contributed equally to this work.

Authors and Affiliations

  1. Guangdong Provincial Key Laboratory of Chiral Molecule and Drug Discovery, School of Pharmaceutical Sciences, Sun Yat-sen University, Guangzhou, 510006, China

    Rimei Zheng, Aimin Xu, Jiawu Huang, Zhijing Zhang, Xinru Yin, Tianyuan Zhang, Wenhao Hu & Yu Qian

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  1. Rimei Zheng
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  2. Aimin Xu
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Correspondence to Yu Qian.

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Zheng, R., Xu, A., Huang, J. et al. A Rh(II)-catalyzed highly stereoselective [3 + 2] annulation of vinyl diazoacetates with indole-2-carbaldehyde for the synthesis of indolyl dihydrofurans. Mol Divers 26, 3379–3386 (2022). https://doi.org/10.1007/s11030-022-10381-0

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