Synthesis 2020; 52(03): 450-458
DOI: 10.1055/s-0039-1690238
paper
© Georg Thieme Verlag Stuttgart · New York

Synthesis of N-(Hetero)arylconvolvine Derivatives through a Palladium-Catalyzed Buchwald–Hartwig Cross-Coupling

Manel Hassine
a   BioCIS-UMR 8076, Univ. Paris-Sud, CNRS, University Paris-Saclay, Châtenay-Malabry, France   eMail: samir.messaoudi@u-psud.fr
b   University of Monastir, Faculty of Science of Monastir, Laboratory of Heterocyclic Chemistry, Natural Products and Reactivity (LR11ES39), Team: Medicinal Chemistry and Natural Products, Avenue of Environment, 5019 Monastir, Tunisia   eMail: hichem.bjannet@gmail.com
,
Hichem Ben Jannet
b   University of Monastir, Faculty of Science of Monastir, Laboratory of Heterocyclic Chemistry, Natural Products and Reactivity (LR11ES39), Team: Medicinal Chemistry and Natural Products, Avenue of Environment, 5019 Monastir, Tunisia   eMail: hichem.bjannet@gmail.com
,
NourEddine Ghermani
c   Institut Galien UMR 8612, Univ. Paris-Sud, CNRS, University Paris-Saclay, Châtenay-Malabry, France
,
Mouad Alami
a   BioCIS-UMR 8076, Univ. Paris-Sud, CNRS, University Paris-Saclay, Châtenay-Malabry, France   eMail: samir.messaoudi@u-psud.fr
,
Samir Messaoudi
a   BioCIS-UMR 8076, Univ. Paris-Sud, CNRS, University Paris-Saclay, Châtenay-Malabry, France   eMail: samir.messaoudi@u-psud.fr
› Institutsangaben
Authors acknowledge support of this project by CNRS, University Paris Sud, and by La Ligue Nationale Contre le Cancer throughout an Equipe Labellisée 2014 grant. The authors are grateful to the Ministry of Higher Education and Scientific Research of Tunisia for financial support. Our laboratory (BioCIS UMR 8076) is a member of the laboratory of excellence LERMIT supported by a grant from ANR (ANR-10-LABX-33).
Weitere Informationen

Publikationsverlauf

Received: 02. Oktober 2019

Accepted after revision: 14. Oktober 2019

Publikationsdatum:
05. November 2019 (online)


Abstract

The present study describes the isolation of convolvine from the roots of the Tunisian plant Convolvulus dorycnium L. and its synthesis through a four-step sequence starting from tropine. Then, an efficient synthesis of N-(het)aryltropanes derivatives by a sequence of a palladium-catalyzed N-arylationof convolvine has been established. This strategy enabled access to unknown tropane scaffolds of biological interests.

Supporting Information

 
  • References

  • 1 Lounasmaa M, Tamminen T. In The Alkaloids, Vol. 44. Cordell GA. Academic Press; New York: 1993: 1
    • 2a Kukula-Koch WA, Widelski J. In Pharmacognosy, Fundamentals, Applications and Strategies . Badal S, Delgoda R. Elsevier; Amsterdam: 2017: 163
    • 2b Grynkiewicz G, Gadzikowska M. Pharmacol. Rep. 2008; 60: 439
  • 3 Grynkiewicz G, Gadzikowska M. Acta Pol. Pharm. 2008; 60: 439
  • 4 Bussenius J, Blazey CM, Aay N, Anand NK, Arcalas A, Baik T, Bowles OJ, Buhr CA, Costanzo S, Curtis JK, DeFina SC, Dubenko L, Heuer TS, Huang P, Jaeger C, Joshi A, Kennedy AR, Kim AI, Lara K, Lee J, Li J, Lougheed JC, Ma S, Malek S, Manalo JC, Martini JF, McGrath G, Nicoll M, Nuss JM, Pack M, Peto CJ, Tsang TH, Wang L, Womble SW, Yakes M, Zhang W, Rice KD. Bioorg. Med. Chem. Lett. 2012; 22: 5396
  • 5 Audisio D, Messaoudi S, Cegielkowski L, Peyrat J.-F, Brion J.-D, Methy-Gonnot D, Radanyi C, Renoir J.-M, Alami M. ChemMedChem 2011; 6: 804
  • 6 Audisio D, Messaoudi S, Peyrat J.-F, Brion J.-D, Alami M. J. Org. Chem. 2011; 76: 4995
  • 7 Yagudaev MR, Aripova SF. Khim. Prir. Soedin. 1986; 80
  • 8 Sharova EG, Aripova SF, Yu Yunusov S. Khim. Prir. Soedin. 1980; 672
    • 9a Aripova SF, Yu Yunusov S. Khim. Prir. Soedin. 1979; 527
    • 9b Aripova SF, Sharova EG, Yu Yunusov S, Dzhabbarov A. Khim. Prir. Soedin. 1983; 245
  • 10 Maksay G, Nemes P, Bíró T. J. Med. Chem. 2004; 47: 6384
  • 11 CCDC 1535462 contains the crystallographic data (excluding structure factors) for the structure of N-methylconvolvine (3) for this paper. The data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/getstructures.
    • 12a Kraiss G, Nádor K. Tetrahedron Lett. 1971; 57
    • 12b Wallace JL, Kidd MR, Cauthen SE, Woodyard JD. J. Pharm. Sci. 1980; 69: 1357
    • 12c Do Pham DD, Kelso GF, Yang Y, Hearn MT. W. Green Chem. 2012; 14: 1189
  • 13 Messaoudi S, Audisio D, Brion J.-D, Alami M. Tetrahedron 2007; 63: 10202