Towards new camptothecins. Part 3: Synthesis of 5-methoxycarbonyl camptothecin |
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Authors: | Thierry Brunin Jean-Pierre Hénichart |
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Institution: | a Ecole des Hautes Etudes Industrielles, 13 rue de Toul, 59046 Lille, France b Institut de Chimie Pharmaceutique Albert Lespagnol, Université de Lille 2, rue du Professeur Laguesse, 59006 Lille, France |
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Abstract: | The synthesis of two camptothecin analogs substituted by a carbonyl function on position 5 of cycle C was realized. New conditions were studied to obtain the E-lactone ring of these heterocycles. These compounds were obtained from the reaction of Bredereck's reagent with indolizines derived from pyroglutamic acid. This yielded dimethylaminovinyl groups whose oxidation by NaIO4 yielded ketones. The indolizinones obtained were reacted in Friedlander condition, to give the scaffold of the desired camptothecins. |
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Keywords: | Camptothecins Mannich reaction Bredereck's reagent |
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