Synthesis 2018; 50(02): 314-322
DOI: 10.1055/s-0036-1590918
paper
© Georg Thieme Verlag Stuttgart · New York

Asymmetric Organocatalytic Cascade Synthesis of Tetrahydro­furanyl Spirooxindoles

Dmitri Trubitsõna, Sergei Žari, a, Sandra Kaabela, Marina Kudrjashovaa, Kadri Kriisa, Ivar Järvinga, Tõnis Pehkb, Tõnis Kanger*a
  • aDepartment of Chemistry and Biotechnology, School of Science, Tallinn University of Technology, Akadeemia tee 15, 12618 Tallinn, Estonia
  • bNational Institute of Chemical Physics and Biophysics, Akadeemia tee 23, 12618 Tallinn, Estonia   Email: tonis.kanger@ttu.ee
The authors thank the Estonian Ministry of Education and Research (grant nos. IUT19-32, IUT19-9, IUT23-7, PUT1468 and PUT692) and the Centre of Excellence in Molecular Cell Engineering (2014-2020.4.01.15-0013) for financial support.
Further Information

Publication History

Received: 20 July 2017

Accepted after revision: 05 September 2017

Publication Date:
18 September 2017 (eFirst)

Dedicated to Professor Victor Snieckus on the occasion of his 80th birthday

Abstract

An enantio- and regioselective organocatalytic cascade starting from isatin has been disclosed to construct tetrahydrofuranyl spirooxindoles in high yields and stereoselectivities. Also, a triple cascade leading to the pentacyclic compound with two quaternary and a tertiary stereocenter is described. The reactions were catalyzed by cinchonine-based thiourea.

Supporting Information

 
  • References

  • 1 Present address: Department of Pathology, Michigan Medicine, University of Michigan, 1150 W. Medical Center Drive, Ann Arbor, Michigan 48109-5605, USA.

    • For recent reviews, see:
    • 2a Yu B. Yu D.-Q. Liu H.-M. Eur. J. Med. Chem. 2015; 97: 673
    • 2b Yu B. Zheng Y.-C. Shi X.-J. Qi P.-P. Liu H.-M. Anti-Cancer Agents Med. Chem. 2016; 16: 1315
    • 2c Ye N. Chen H. Wold EA. Shi P.-Y. Zhou J. ACS Infect. Dis. 2016; 2: 38
    • 2d Pavlovska TL. Redkin RGr. Lipson VV. Atamanuk DV. Mol. Divers. 2016; 20: 299

      For recent reviews, see:
    • 3a Yan L.-J. Wang Y.-C. ChemistrySelect 2016; 1: 6948
    • 3b Ball-Jones NR. Badillo JJ. Franz AK. Org. Biomol. Chem. 2012; 10: 5165
    • 3c Santos MM. M. Tetrahedron 2014; 70: 9735
    • 4a Cheng D. Ishihara Y. Tan B. Barbas CF. III. ACS Catal. 2014; 4: 743
    • 4b Grondal C. Jeanty M. Enders D. Nat. Chem. 2010; 2: 167
    • 4c Tan B. Candeias NR. Barbas CF. III. Nat. Chem. 2011; 3: 473

      Selected examples:
    • 5a Kobayashi K. Ohshiro T. Tomoda T. Yin F. Cui H.-L. Chouthaiwale PV. Tanaka F. Bioorg. Med. Chem. Lett. 2016; 26: 5899
    • 5b Cui H.-L. Chouthaiwale PV. Yin F. Tanaka F. Org. Biomol. Chem. 2016; 14: 1777
    • 5c Cao J. Dong S. Jiang D. Zhu P. Zhang H. Li R. Li Z. Wang X. Tang W. Du D. J. Org. Chem. 2017; 82: 4186
    • 5d Alcaide B. Almendros P. Luna A. Gómez-Campillos G. Torres MR. J. Org. Chem. 2012; 77: 3549
  • 6 Silvi M. Chatterjee I. Liu Y. Melchiorre P. Angew. Chem. Int. Ed. 2013; 52: 10780
  • 7 Liu Y.-L. Wang X. Zhao Y.-L. Zhu F. Zeng X.-P. Chen L. Wang C.-H. Zhao X.-L. Zhou J. Angew. Chem. Int. Ed. 2013; 52: 13735
  • 8 Liu H. Wu H. Luo Z. Shen J. Kang G. Liu B. Wan Z. Jiang J. Chem. Eur. J. 2012; 18: 11899
  • 9 Zhang Y. Lu Y. Tang W. Lu T. Du D. Org. Biomol. Chem. 2014; 12: 3009
  • 10 Kumarswamyreddy N. Kesavan V. Eur. J. Org. Chem. 2016; 5301
  • 11 Zhang D. Johnson S. Cui H.-L. Tanaka F. Asian J. Org. Chem. 2014; 3: 391
  • 12 Singh GS. Desta ZY. Chem. Rev. 2012; 112: 6104
  • 13 Hayes SJ. Knight DW. Smith AW. T. O’Halloran MJ. Tetrahedron Lett. 2010; 51: 720
    • 14a Metsala A. Žari S. Kanger T. ChemCatChem 2016; 8: 2961
    • 14b Žari S. Metsala A. Kudrjashova M. Kaabel S. Järving I. Kanger T. Synthesis 2015; 47: 875
    • 14c Žari S. Kudrjashova M. Pehk T. Lopp M. Kanger T. Org. Lett. 2014; 16: 1740
    • 14d Ošeka M. Noole A. Žari S. Öeren M. Järving I. Lopp M. Kanger T. Eur. J. Org. Chem. 2014; 3599
    • 14e Žari S. Kailas T. Kudrjashova M. Öeren M. Järving I. Tamm T. Lopp M. Kanger T. Beilstein J. Org. Chem. 2012; 8: 1452
    • 15a Noole A. Ošeka M. Pehk T. Öeren M. Järving I. Elsegood MR. J. Malkov AV. Lopp M. Kanger T. Adv. Synth. Catal. 2013; 355: 829
    • 15b Noole A. Ilmarinen K. Järving I. Lopp M. Kanger T. J. Org. Chem. 2013; 78: 8117
    • 15c Noole A. Järving I. Werner F. Lopp M. Malkov A. Kanger T. Org. Lett. 2012; 14: 4922
    • 15d Noole A. Sucman NS. Kabeshov MA. Kanger T. Macaev FZ. Malkov AV. Chem. Eur. J. 2012; 18: 14929
  • 16 Vakulya B. Varga S. Csámpai A. Soós T. Org. Lett. 2005; 7: 1967
  • 17 Tomotaka O. Hoashi Y. Takemoto Y. J. Am. Chem. Soc. 2003; 125: 12672