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
› Author Affiliations
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).
Further Information

Publication History

Received: 02 October 2019

Accepted after revision: 14 October 2019

Publication Date:
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

 
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