Two versatile routes towards Cerpegin and analogues: applications of a one pot reaction to new analogues of Cerpegin |
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Authors: | Didier Villemin Nawel Cheikh Liang Liao Nathalie Bar Jean-François Lohier Jana Sopkova Noureddine Choukchou-Braham Bachir Mostefa-Kara |
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Institution: | 1. Laboratoire de Chimie Moléculaire et Thioorganique (LCMT), UMR CNRS 6507, INC3M, FR 3038, Labex EMC3, ENSICAEN & Université de Caen, 14050 Caen, France;2. Laboratoire de Catalyse et Synthèse en Chimie Organique, Dept de Chimie, Faculté des Sciences, Université Abou Bekr Belkaid, BP 119, Tlemcen 13000, Algeria;3. Centre d''Etudes et de Recherche sur le Médicament de Normandie (CERMN), Université de Caen, 5 rue Vaubénard, F-14032 Caen, France |
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Abstract: | Simple and efficient routes to the natural alkaloid Cerpegin and new analogues are described herein. In a first approach, we extend the scope of a one pot three steps reaction, which permits the synthesis of new analogues of Cerpegin, substituted in different ways. In a second line of approach, we present an unprecedented synthesis of Cerpegin and analogues where methylfuranones are condensed with dimethylformamide diethylacetal (DMFDEA) to yield enaminolactone esters, which react easily with various primary amines affording Cerpegin and new analogues. We applied this second approach to the synthesis of new bis-Cerpegins and N-amino-Cerpegins. Most of the syntheses are performed under environmental friendly conditions. |
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