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Theses

Synthèse de l'analogue benzoxazinique de l'ellipticine.
Synthèse et réactivité de bis-vinylphosphates dérivés d'imides

Abstract : Ellipticine, a representative member of pyrido[4,3-b] carbazole alkaloids, is highly cytotoxic
because of its intercaling properties and also because of its ability to inhibit DNA relegation
activity of the topoisomerase II. A large number of laboratories are invested in the
development of new efficient synthetic strategies of ellipticine and analogues.
In the first part of my work, by using a methodology previously reported by our group, we
have developed an access to a new benzoxazinic analogue of ellipticine in 9 steps and in 4%
global yield. The key step of our strategy allowed the formation of the tetracyclic skeleton by
the condensation of the N-Boc protected 1,4-benzoxazine with the N,N-diethyl-4-
formylnicotinamide according to a double reaction of metallation. The introduction of various
substituents is then realized by using palladium cross-coupling reactions.
In a second part, we have described the preparation of original 1,4-dihydropyridines
substituted in position 2 and 6 by a range of alkenyl, allyl, aryl or heteroaryl groups by using a
Suzuki-Miyaura or Stille cross-coupling reactions on glutarimide derived bis-vinylphosphates.
In addition, we optimized the alkylation reaction on the C-4 position of the dihydropyridines.
By acidic treatment of substituted 1,4-dihydropyridines, we obtained, according to
experimental conditions, various substituted original pyridines or open diketonic compounds.
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Deborah Mousset. Synthèse de l'analogue benzoxazinique de l'ellipticine.
Synthèse et réactivité de bis-vinylphosphates dérivés d'imides. Autre. Université d'Orléans, 2005. Français. ⟨tel-00168376⟩

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