Towards new camptothecins. Part 3: Synthesis of 5-methoxycarbonyl camptothecin

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 fro...

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Bibliographic Details
Published in:Tetrahedron 2006-04, Vol.62 (17), p.3959-3968
Main Authors: Brunin, Thierry, Legentil, Laurent, Hénichart, Jean-Pierre, Rigo, Benoît
Format: Article
Language:English
Subjects:
Bredereck's reagent
Camptothecins
Mannich reaction
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Summary: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 NaIO 4 yielded ketones. The indolizinones obtained were reacted in Friedlander condition, to give the scaffold of the desired camptothecins. The synthesis of two camptothecin analogs substituted by a carbonyl function on position 5 of cycle C was realized.
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2006.02.034