Download PDF
Synthesis 2022; 54(08): 1977-1982
DOI: 10.1055/s-0041-1737339
feature

Total Synthesis of (+)-Kingianin A by Enantioselective Cycloaddition of Strained Cyclobutenone

Jie Zhang
a   Department of Chemistry and Biology, Jilin Provincial Key Laboratory of Carbon Fiber Development and Application, Changchun University of Technology, Changchun 130012, P. R. of China
,
Peng Yan
b   Research Center for Molecular Recognition and Synthesis, Department of Chemistry, Fudan University, 220 Handan Lu, Shanghai 200433, P. R. of China
,
Zhichao Wang
b   Research Center for Molecular Recognition and Synthesis, Department of Chemistry, Fudan University, 220 Handan Lu, Shanghai 200433, P. R. of China
,
Jinbo Zhao∗
a   Department of Chemistry and Biology, Jilin Provincial Key Laboratory of Carbon Fiber Development and Application, Changchun University of Technology, Changchun 130012, P. R. of China
,
Qin Chen∗
b   Research Center for Molecular Recognition and Synthesis, Department of Chemistry, Fudan University, 220 Handan Lu, Shanghai 200433, P. R. of China
,
Ping Lu  ∗
b   Research Center for Molecular Recognition and Synthesis, Department of Chemistry, Fudan University, 220 Handan Lu, Shanghai 200433, P. R. of China
› Author AffiliationsWe are grateful for the financial support from the National Natural Science Foundation of China (22071028, 21772024, 21921003).
› Further Information
    Permissions and Reprints All articles of this category


Abstract

We report here the first asymmetric total synthesis of (+)-kingianin A via dimerization of an enantioenriched bicyclo[4.2.0]octadiene. The synthesis features a chiral oxazaborolidinium ion catalyzed Diels–Alder reaction of strained cyclobutenone and stereoselective functionalization of the cyclobutane ring. A preliminary biological study indicated that (+)-kingianin A exhibits potent anticancer activities.

Key words

cyclobutenone - chiral oxazaborolidinium ion - Diels–Alder reaction - strain-release driven - bicyclo[4.2.0]octanes - kingianins

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0041-1737339.
  • Supporting Information


Publication History

Received: 09 November 2021

Accepted: 08 December 2021

Article published online:
08 February 2022

© 2022. Thieme. All rights reserved

Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany

 

  • References

    • 1a Sinninghe Damsté JS, Strous M, Rijpstra WI. C, Hopmans EC, Geenevasen JA. J, van Duin AC. T, van Niftrik LA, Jetten MS. M. Nature 2002; 419: 708
      CrossrefPubMed
    • 1b Sinninghe Damsté JS, Rijpstra WI. C, Geenevasen JA. J, Strous M, Jetten MS. M. FEBS J. 2005; 272: 4270
      CrossrefPubMed
    • 2a Siengalewicz P, Mulzer J, Rinner U. Eur. J. Org. Chem. 2011; 7041
      Crossref
    • 2b Xie S, Wu Y, Qiao Y, Guo Y, Wang J, Hu Z, Zhang Q, Li X, Huang J, Zhou Q, Luo Z, Liu J, Zhu H, Xue Y, Zhang Y. J. Nat. Prod. 2018; 81: 1311
      CrossrefPubMed
    • 3a Leverrier A, Dau ME. T. H, Retailleau P, Awang K, Guéritte F, Litaudon M. Org. Lett. 2010; 12: 3638
      CrossrefPubMed
    • 3b Leverrier A, Awang K, Guéritte F, Litaudon M. Phytochemistry 2011; 72: 1443
      CrossrefPubMed
    • 3c Azmi MN, Peresse T, Remeur C, Chan G, Roussi F, Litaudon M, Awang K. Fitoterapia 2016; 109: 190
      CrossrefPubMed
    • 4a Drew SL, Lawrence AL, Sherburn MS. Angew. Chem. Int. Ed. 2013; 52: 4221
      CrossrefPubMed
    • 4b Drew SL, Lawrence AL, Sherburn MS. Chem. Sci. 2015; 6: 3886
      CrossrefPubMed
    • 6a Sharma P, Ritson DJ, Burnley J, Moses JE. Chem. Commun. 2011; 47: 10605
      CrossrefPubMed
    • 6b Moore JC, Davies ES, Walsh DA, Sharma P, Moses JE. Chem. Commun. 2014; 50: 12523
      CrossrefPubMed
    • 7a Wang M, Zhong C, Lu P. Synlett 2021; 32: 1253
      Article in Thieme Connect
    • 7b Wang M, Chen J, Chen Z, Zhong C, Lu P. Angew. Chem. Int. Ed. 2018; 57: 2707
      CrossrefPubMed
    • 7c Zhong C, Huang Y, Zhang H, Zhou Q, Liu Y, Lu P. Angew. Chem. Int. Ed. 2020; 59: 2750
      CrossrefPubMed
    • 7d Zhong C, Wang SW, Lu P. Org. Chem. Front. 2021; 8: 2977
      Crossref
  • 8 Ryu DH, Lee TW, Corey EJ. J. Am. Chem. Soc. 2002; 124: 9992
    CrossrefPubMed
  • 9 Yan P, Zhong C, Zhang J, Liu Y, Fang H, Lu P. Angew. Chem. Int. Ed. 2021; 60: 4609
    CrossrefPubMed
  • 10 Vrielynck F, Van Haver D, Vandewalle M, Verlinden L, Verstuyf A, Bouillon R, Croce G, DeClercq P. Eur. J. Org. Chem. 2009; 1720
    Crossref
  • 11 Deutsch C, Krause N, Lipshutz BH. Chem. Rev. 2008; 108: 2916
    CrossrefPubMed
  • 12 Bell F, Ledwith A, Sherrington D. J. Chem. Soc. C 1969; 2719
    Crossref