One-pot multicomponent construction of chromanone-fused pyrrolidinyl spirooxindole collections through a decarboxylative 1,3-dipolar [3 + 2] cycloaddition reaction

References

• (a) Nicolaou, K. C.; Edmonds, D. J.; Bulger, P. G. Cascade Reactions in Total Synthesis. Angew. Chem. Int. Ed. 2006, 45, 7134–7186. DOI: 10.1002/anie.200601872.
   PubMed Web of Science ®Google Scholar
  (b) Newman, D. J.; Cragg, G. M. Natural Products as Sources of New Drugs over the Last 25 Years. J. Nat. Prod. 2007, 70, 461–477. DOI: 10.1021/np068054v.
   PubMed Web of Science ®Google Scholar
  (c) Li, J. W. H.; Vederas, J. C. Drug Discovery and Natural Products: End of an Era or an Endless Frontier? Science 2009, 325, 161–165. DOI: 10.1126/science.1168243.
   PubMed Web of Science ®Google Scholar
  (d) Ding, K.; Lu, Y.; Coleska, N. Z.; Qiu, S.; Ding, Y.; Gao, W.; Stuckey, J.; Krajewski, K.; Roller, P. P.; Tomita, Y.; et al. Structure-Based Design of Potent Non-Peptide MDM2 Inhibitors. J. Am. Chem. Soc. 2005, 127, 10130–10131. DOI: 10.1021/ja051147z.
   PubMed Web of Science ®Google Scholar
  (e) Ma, C.; Jiang, F.; Sheng, F.-T.; Jiao, Y.; Mei, G.-J.; Shi, F. Design and Catalytic Asymmetric Construction of Axially Chiral 3,3'-Bisindole Skeletons. Angew. Chem. Int. Ed. Engl. 2019, 58, 3014–3020. DOI: 10.1002/anie.201811177.
   PubMed Web of Science ®Google Scholar
  (f) Ma, C.; Zhou, J.-Y.; Zhang, Y.-Z.; Jiao, Y.; Mei, G.-J.; Shi, F. Synergistic-Catalysis-Enabled Reaction of 2-Indolymethanols with Oxonium Ylides for the Construction of 3-Indolyl-3-Alkoxy Oxindole Frameworks. Chem. Asian J. 2018, 13, 2549–2558. DOI: 10.1002/asia.201800620.
   PubMed Web of Science ®Google Scholar
  (g) Zeng, X.-P.; Zhou, J. Me2(CH2Cl)SiCN: Bifunctional Cyanating Reagent for the Synthesis of Tertiary Alcohols with a Chloromethyl Ketone Moiety via Ketone Cyanosilylation. J. Am. Chem. Soc. 2016, 138, 8730–8733. DOI: 10.1021/jacs.6b05601.
   PubMed Web of Science ®Google Scholar
• (a) Cheng, D.; Ishihara, Y.; Tan, B.; Barbas, C. F. III Organocatalytic Asymmetric Assembly Reactions: Synthesis of Spirooxindoles via Organocascade Strategies. ACS Catal. 2014, 4, 743–762. DOI: 10.1021/cs401172r.
   Web of Science ®Google Scholar
  (b) Singh, G. S.; Desta, Z. Y. Isatins as Privileged Molecules in Design and Synthesis of Spiro-Fused Cyclic Frameworks. Chem. Rev. 2012, 112, 6104–6155. DOI: 10.1021/cr300135y.
   PubMed Web of Science ®Google Scholar
  (c) Hong, L.; Wang, R. Recent Advances in Asymmetric Organocatalytic Construction of 3,3’-Spirocyclic Oxindoles. Adv. Synth. Catal. 2013, 355, 1023–1052. DOI: 10.1002/adsc.201200808.
   Web of Science ®Google Scholar
  (d) Yu, B.; Zheng, Y. C.; Shi, X. J.; Qi, P. P.; Liu, H. M. Natural Product-Derived Spirooxindole Fragments Serve as Privileged Substructures for Discovery of New Anticancer Agents. Anti-Canc. Agent. Med. Chem. 2016, 16, 1315–1324. DOI: 10.2174/1871520615666151102093825.
   PubMed Web of Science ®Google Scholar
  (e) Han, W. Y.; Zhao, J. Q.; Zuo, J.; Xu, X. Y.; Zhang, X. M.; Yuan, W. C. Recent Advances of α-Isothiocyanato Compounds in the Catalytic Asymmetric Reaction. Adv. Synth. Catal. 2015, 357, 3007–3031. DOI: 10.1002/adsc.201500264.
   Web of Science ®Google Scholar
  (f) Zhou, F.; Liu, Y. L.; Zhou, J. Catalytic Asymmetric Synthesis of Oxindoles Bearing a Tetrasubstituted Stereocenter at the C-3 Position. Adv. Synth. Catal. 2010, 352, 1381–1407. DOI: 10.1002/adsc.201000161.
   Web of Science ®Google Scholar
  (g) Mei, G.; Shi, F. Catalytic Asymmetric Synthesis of Spirooxindoles: Recent Developments. Chem. Commun. (Camb.) 2018, 54, 6607–6621. DOI: 10.1039/C8CC02364F.
   PubMed Web of Science ®Google Scholar
  (h) Cao, Z.-Y.; Zhou, F.; Zhou, J. Development of Synthetic Methodologies via Catalytic Enantioselective Synthesis of 3,3-Disubstituted Oxindoles. Acc. Chem. Res. 2018, 51, 1443–1454. DOI: 10.1021/acs.accounts.8b00097.
   PubMed Web of Science ®Google Scholar
• (a) Suman, K.; Srinu, L.; Thennarasu, S. Lewis Acid Catalyzed Unprecedented [3 + 2] Cycloaddition Yields 3,3′-Pyrrolidinyldispirooxindoles Containing Four Contiguous Chiral Stereocenters with Two Contiguous Quaternary Spirostereocenters. Org. Lett. 2014, 16, 3732–3735. DOI: 10.1021/ol501547p.
   PubMed Web of Science ®Google Scholar
  (b) Han, Y.-Y.; Chen, W.-B.; Han, W.-Y.; Wu, Z.-J.; Zhang, X.-M.; Yuan, W.-C. Highly Efficient and Stereoselective Construction of Dispiro-[Oxazolidine-2-Thione]Bisoxindoles and Dispiro[Imidazolidine-2-Thione]Bisoxindoles. Org. Lett. 2012, 14, 490. DOI: 10.1021/ol203081x.
   PubMed Web of Science ®Google Scholar
  (c) He, Q.; Du, W.; Chen, Y.-C. Asymmetric [3 + 2] Annulations to Construct 1,2-Bispirooxindoles Incorporating a Dihydropyrrolidine Motif. Adv. Synth. Catal. 2017, 359, 3782. DOI: 10.1002/adsc.201700849.
   Web of Science ®Google Scholar
  (d) Huang, W.-J.; Chen, Q.; Lin, N.; Long, X.-W.; Pan, W.-G.; Xiong, Y.-S.; Weng, J.; Lu, G. Asymmetric Synthesis of Trifluoromethyl-Substituted 3,3’-Pyrrolidinyl-Dispirooxindoles through Organocatalytic 1,3-dipolar Cycloaddition Reactions. Org. Chem. Front. 2017, 4, 472.
   Web of Science ®Google Scholar
  (e) Zhao, K.; Zhi, Y.; Li, X.; Puttreddy, R.; Rissanen, K.; Enders, D. Asymmetric Synthesis of 3,3'-pyrrolidinyl-dispirooxindoles via a One-Pot Organocatalytic Mannich/Deprotection/Aza-Michael Sequence. Chem. Commun. (Camb.) 2016, 52, 2249. DOI: 10.1039/C5CC10057G.
   PubMed Web of Science ®Google Scholar
  (f) Liu, Y.-L.; Wang, X.; Zhao, Y.-L.; Zhu, F.; Zeng, X.-P.; Chen, L.; Wang, C.-H.; Zhao, X.-L.; Zhou, J. One-pot tandem approach to spirocyclic oxindoles featuring adjacent spiro-stereocenters. Angew. Chem. Int. Ed. Engl. 2013, 52, 13735. DOI: 10.1002/anie.201307250.
   PubMed Web of Science ®Google Scholar
  (g) Chen, Y.; Cui, B.-D.; Wang, Y.; Han, W.-Y.; Wan, N.-W.; Bai, M.; Yuan, W.-C.; Chen, Y.-Z. Asymmetric [3 + 2] Cycloaddition Reaction of Isatin-Derived MBH Carbonates with 3-Methyleneoxindoles: Enantioselective Synthesis of 3,3′-Cyclopentenyldispirooxindoles Incorporating Two Adjacent Quaternary Spirostereocenters. J. Org. Chem. 2018, 83, 10465. DOI: 10.1021/acs.joc.8b01506.
   PubMed Web of Science ®Google Scholar
  (h) Cui, B.-D.; Han, W.-Y.; Wu, Z.-J.; Zhang, X.-M.; Yuan, W.-C. Enantioselective Synthesis of Quaternary 3-Aminooxindoles via Organocatalytic Asymmetric Michael Addition of 3-Monosubstituted 3-Aminooxindoles to Nitroolefins. J. Org. Chem. 2013, 78, 8833–8839. DOI: 10.1021/jo401154b.
   PubMed Web of Science ®Google Scholar
  (i) Zhu, Y.; Guo, J.; Jin, S.; Guo, J.; Bai, X.; Wang, Q.; Bu, Z. Construction of Bridged Cyclic N,O-Ketal Spirooxindoles through a Michael Addition/N,O-Ketalization Sequence. Org. Biomol. Chem. 2018, 16, 1751–1759. DOI: 10.1039/C8OB00306H.
   PubMed Web of Science ®Google Scholar
  (j) Zhu, Y.-S.; Wang, W.-B.; Yuan, B.-B.; Li, Y.-N.; Wang, Q.-L.; Bu, Z.-W. A DBU-Catalyzed Michael-Pinner-Isomerization Cascade Reaction of 3-Hydroxyoxindoles with Isatylidene Malononitriles: Access to Highly Functionalized Bispirooxindoles Containing a Fully Substituted Dihydrofuran Motif. Org. Biomol. Chem. 2017, 15, 984–990. DOI: 10.1039/C6OB02254E.
   PubMed Web of Science ®Google Scholar
  (k) Zhu, Y.; Zhou, J.; Jin, S.; Dong, H.; Guo, J.; Bai, X.; Wang, Q.; Bu, Z. Metal-Free Diastereoselective Construction of Bridged Ketal Spirooxindoles via a Michael Addition-Inspired Sequence. Chem. Commun. (Camb.) 2017, 53, 11201–11204. DOI: 10.1039/C7CC05813F.
   PubMed Web of Science ®Google Scholar
  (l) Guo, J.; Zhao, Y.; Fang, D.; Wang, Q.; Bu, Z. Diastereoselective Construction of Pyrrolo[2,1-a]Isoquinoline-Based Bispirooxindoles through a Three-Component [3 + 2] Cycloaddition. Org. Biomol. Chem. 2018, 16, 6025–6034. DOI: 10.1039/C8OB01493K.
   PubMed Web of Science ®Google Scholar
  (m) Guo, J.; Bai, X.; Wang, Q.; Bu, Z. Diastereoselective Construction of Indole-Bridged Chroman Spirooxindoles through a TfOH-Catalyzed Michael Addition-Inspired Cascade Reaction. J. Org. Chem. 2018, 83, 3679–3687. DOI: 10.1021/acs.joc.8b00035.
   PubMed Web of Science ®Google Scholar
  (n) Xu, P.-W.; Liu, J.-K.; Shen, L.; Cao, Z.-Y.; Zhao, X.-L.; Yan, J.; Zhou, J. Diastereo- and Enantioselective [3 + 3] Cycloaddition of Spirocyclopropyl Oxindoles Using Both Aldonitrones and Ketonitrones. Nat. Commun. 2017, 8, 1619. DOI: 10.1038/s41467-017-01451-1.
   PubMed Web of Science ®Google Scholar
  (o) Yu, J.-S.; Liao, F.-M.; Gao, W.-M.; Liao, K.; Zuo, R.-L.; Zhou, J. Michael Addition Catalyzed by Chiral Secondary Amine Phosphoramide Using Fluorinated Silyl Enol Ethers: Formation of Quaternary Carbon Stereocenters. Angew. Chem. Int. Ed. Engl. 2015, 54, 7381–7385. DOI: 10.1002/anie.201501747.
   PubMed Web of Science ®Google Scholar
  (p) Yin, X.-P.; Zeng, X.-P.; Liu, Y.-L.; Liao, F.-M.; Yu, J.-S.; Zhou, F.; Zhou, J. Asymmetric Triple Relay Catalysis: enantioselective Synthesis of Spirocyclic Indolines through a one-pot process featuring an asymmetric 6π electrocyclization. Angew. Chem. Int. Ed. Engl. 2014, 53, 13740–13745. DOI: 10.1002/anie.201407677.
   PubMed Web of Science ®Google Scholar
  (q) Cao, Z.-Y.; Wang, X.; Tan, C.; Zhao, X.-L.; Zhou, J.; Ding, K. Highly Stereoselective Olefin Cyclopropanation of Diazooxindoles Catalyzed by a C2-Symmetric Spiroketal Bisphosphine/Au(I) Complex. J. Am. Chem. Soc. 2013, 135, 8197–8200. DOI: 10.1021/ja4040895.
   PubMed Web of Science ®Google Scholar
• (a) Lin, N.; Long, X.; Chen, Q.; Zhu, W.; Wang, B.; Chen, K.; Jiang, C.; Weng, J.; Lu, G. Highly Efficient Construction of Chiral Dispirocyclic Oxindole/Thiobutyrolactam/Chromanone Complexes through Michael/Cyclization Cascade Reactions with a Rosin-Based Squaramide Catalyst. Tetrahedron 2018, 74, 3734–3741. DOI: 10.1016/j.tet.2018.05.052.
   Web of Science ®Google Scholar
  (b) Zhao, B.; Du, D. Chiral-Squaramide-Catalyzed Sulfa-Michael/Aldol Cascade Reactions for Asymmetric Synthesis of Spirothiochromanones. Asian J. Org. Chem. 2015, 4, 778–787. DOI: 10.1002/ajoc.201500171.
   Web of Science ®Google Scholar
  (c) Ren, Q.; Gao, Y.; Wang, J. Enantioselective Synthesis of Densely Functionalized Pyranochromenes via an Unpredictable Cascade Michael-Oxa-Michael-Tautomerization Sequence. Chem. Eur. J. 2010, 16, 13594–13598. DOI: 10.1002/chem.201002490.
   PubMed Web of Science ®Google Scholar
  (d) Gao, Y.; Ren, Q.; Wu, H.; Li, M.; Wang, J. Enantioselective Heterocyclic Synthesis of Spiro Chromanone-Thiochroman Complexes Catalyzed by a Bifunctional Indane Catalyst. Chem. Commun. (Camb.) 2010, 46, 9232–9234. DOI: 10.1039/c0cc03489d.
   PubMed Web of Science ®Google Scholar
  (e) Zhao, L.; Li, S.; Wang, L.; Yu, S.; Raabe, G.; Enders, D. Asymmetric Synthesis of Cyclopentene-Fused Tetrahydroquinolines via N-Heterocyclic Carbene Catalyzed Domino Reactions. Synthesis 2018, 50, 2523–2532.
   Web of Science ®Google Scholar
• For selected examples, see: (a) Emami, S.; Ghanbarimasir, Z. Recent Advances of Chroman-4-One Derivatives: synthetic Approaches and Bioactivities. Eur. J. Med. Chem. 2015, 93, 539–563. DOI: 10.1016/j.ejmech.2015.02.048.
   PubMed Web of Science ®Google Scholar
  (b) Manian, R. D. R. S.; Selva Kumar, S.; Jayashankaran, J.; Raghunathan, R. A Novel Entry to Dispiropyrrolo-Bicyclo[2.2.1]Heptanes through Sequential 1,3-Dipolar and Diels–Alder Cycloaddition Reactions. Tetrahedron Lett. 2006, 47, 829–832. DOI: 10.1016/j.tetlet.2005.11.089.
   Web of Science ®Google Scholar
  (c) Swaroop, P. S.; Raut, G. N.; Gonnade, R. G.; Verma, P.; Gokhale, R. S.; Reddy, D. S. Antituberculosis Agent Diaportheone B: Synthesis, Absolute Configuration Assignment, and anti-TB Activity of Its Analogues. Org. Biomol. Chem. 2012, 10, 5385–5394. DOI: 10.1039/c2ob25831e.
   PubMed Web of Science ®Google Scholar
  (d) Xiong, D.; Zhou, W.; Lu, Z.; Zeng, S.; Wang, J. A Highly Enantioselective Access to Chiral Chromanones and Thiochromanones via Copper-Catalyzed Asymmetric Conjugated Reduction of Chromones and Thiochromones. Chem. Commun. (Camb.) 2017, 53, 6844–6847. DOI: 10.1039/C7CC03939E.
   PubMed Web of Science ®Google Scholar
  (e) Vijayan, A.; Baiju, T.V.; Jijy, E.; Prakash, P.; Shimi, M.; Joseph, N.; Pihko, P. M.; Varughese, S.; Radhakrishnan, K.V. An Easy Access to Fused Chromanones via Rhodium Catalyzed Oxidative Coupling of Salicylaldehydes with Heterobicyclic Olefins. Tetrahedron 2016, 72, 4007–4015. DOI: 10.1016/j.tet.2016.05.031.
   Web of Science ®Google Scholar
  (f) Nugroho, A. E.; Sasaki, T.; Kaneda, T. A.; Hadi, H. A.; Morita, H. Calofolic Acids A-F, Chromanones from the Bark of Calophyllum scriblitifolium with Vasorelaxation Activity. Bioorg. Med. Chem. Lett. 2017, 27, 2124–2128. DOI: 10.1016/j.bmcl.2017.03.071.
   PubMed Web of Science ®Google Scholar
  (g) Bungihan, M. E.; Tan, M. A.; Kitajima, M.; Kogure, N.; Franzblau, S. G.; Dela Cruz, T. E. E.; Takayama, H.; Nonato, M. G. Bioactive Metabolites of Diaporthe sp. P133, an Endophytic Fungus Isolated from Pandanus amaryllifolius. J. Nat. Med. 2011, 65, 606. DOI: 10.1007/s11418-011-0518-x.
   PubMed Web of Science ®Google Scholar
  (h) Ding, B.; Wang, Z.; Xia, G.; Huang, X.; Xu, F.; Chen, W.; She, Z. Three New Chromone Derivatives Produced by Phomopsis sp. HNY29-2B from Acanthus ilicifolius Linn. Chin. J. Chem. 2017, 35, 1889–1893. DOI: 10.1002/cjoc.201700375.
   Web of Science ®Google Scholar
• Padwa, A.; Pearson, W. H. In Synthetic Applications of 1,3-Dipolar Cycloaddition Chemistry Toward Heterocycles and Natural Products; Wiley: New York, NY, 2002; Vol. 59, pp 169.
   Google Scholar
• (a) Yue, J.; Chen, S.; Zuo, X.; Liu, X.-L.; Xu, S.-W.; Zhou, Y. Diversity-Oriented One-Pot Multicomponent Synthesis of Chromanone-Based 3,3′-Pyrrolidinyl-Spirooxindoles via a 1,3-Dipolar Cycloaddition Reaction. Tetrahedron Lett. 2019, 60, 137–141. DOI: 10.1016/j.tetlet.2018.11.075.
   Web of Science ®Google Scholar
  (b) Liu, X.-W.; Yao, Z.; Yang, J.; Chen, Z.-Y.; Liu, X.-L.; Zhao, Z.; Lu, Y.; Zhou, Y.; Cao, Y. 1,3-Dipolar Cycloaddition Enabled Isoxazole-Fused Spiropyrrolidine Oxindoles Syntheses from 3-Methyl-4-Nitro-5-Alkenyl-Isoxazoles and Azomethine Ylides. Tetrahedron 2016, 72, 1364–1374. DOI: 10.1016/j.tet.2016.01.029.
   Web of Science ®Google Scholar
  (c) Yang, J.; Liu, X.-W.; Wang, D.-D.; Tian, M.-Y.; Han, S.-N.; Feng, T.-T.; Liu, X.-L.; Mei, R.-Q.; Zhou, Y. Diversity-Oriented One-Pot Multicomponent Synthesis of Spirooxindole Derivatives and Their Biological Evaluation for Anticancer Activities. Tetrahedron 2016, 72, 8523–8536. DOI: 10.1016/j.tet.2016.10.050.
   Web of Science ®Google Scholar
  (d) Liu, X.-L.; Chang, S.-Q.; Jiang, Y.; Xu, S.-W.; Zuo, X.; Chen, S.; Tian, M.-Y. Highly Diastereo-, α-Regioselective Catalyst-Free Construction of Adjacent Dispirobisoxindoles with Three Contiguous Quaternary Carbon Centers. Synthesis 2019, 51, 683–692.
   Web of Science ®Google Scholar
  (e) Liu, X.-L.; Han, W.-Y.; Zhang, X.-M.; Yuan, W.-C. Highly Efficient and Stereocontrolled Construction of 3,3′-Pyrrolidonyl Spirooxindoles via Organocatalytic Domino Michael/Cyclization Reaction. Org. Lett. 2013, 12, 1246–1249.
   Web of Science ®Google Scholar
  (f) Feng, T.-T.; Gong, Y.; Wei, Q.-D.; Wang, G.-L.; Liu, H.-H.; Tian, M.-Y.; Liu, X.-L.; Chen, Z.-Y.; Zhou, Y. Diversity-Oriented Construction of Chromanone-Fused Polycyclic Pyrrolidinyl-Dispirooxindoles. J. Heterocyclic Chem. 2018, 55, 1136–1146. DOI: 10.1002/jhet.3145.
   Web of Science ®Google Scholar
  (g) Liu, X.-L.; Zhou, G.; Gong, Y.; Yao, Z.; Zuo, X.; Zhang, W.-H.; Zhou, Y. Stereocontrolled Synthesis of Bispirooxindole-Based Hexahydroxanthones with Five Contiguous Stereocenters. Org. Lett. 2019, 21, 2528–2531. DOI: 10.1021/acs.orglett.9b00139.
   PubMed Web of Science ®Google Scholar
• Access Structures. Cambridge Crystallographic Data Centre. www.ccdc.cam.ac.uk/data_request/cif.
   Google Scholar
• (a) Mosman, T. J. Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays. Immunol. Meth. 1983, 65, 55–63.
   Google Scholar
  (b) Alley, M. C.; Scudiero, D. A.; Monks, A.; Hursey, M. L.; Czerwinski, M. J.; Fine, D. L.; Abbott, B. J.; Mayo, J. G.; Shoemaker, R. H.; Boyd, M. R. Feasibility of Drug Screening with Panels of Human Tumor Cell Lines Using a Microculture Tetrazolium Assay. Cancer Res. 1988, 48, 589–601.
   PubMed Web of Science ®Google Scholar