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Methyl 4-(1-methylpyrrolidin-2-yl)-3-oxobutanoate and hygrine are important biosynthetic intermediates for tropane alkaloids. We have developed a concise method to synthesize these two compounds from the key intermediate N-methylpyrrolinium cation. Methyl 4-(1-methylpyrrolidin-2-yl)-3-oxobutanoate and hygrine were obtained in four and six steps from commercially available 4,4-diethoxybutylamine with overall yields of 42% and 25%, respectively. Key words: methyl 4-(1-methylpyrrolidin-2-yl)-3-oxobutanoate, hygrine, biosynthetic intermediate, tropane alkaloid, N-methylpyrrolinium cation. Le 4-(1-methylpyrrolidin-2-yl)-3-oxobutanoate de methyle et l'hygrine sont des intermediaires biosynthetiques importants pour la synthese des alcaloides tropaniques. Nous avons mis au point une methode pour synthetiser ces deux composes tk;4a partir du cation N-methylpyrrolinium comme intermediaire cle. Nous avons obtenu le 4-(1-methylpyrrolidin-2-yl)-3-oxobutanoate de methyle et l'hygrine en quatre et six etapes, respectivement, a partir de la 4,4-diethoxybutylamine, qui est commercialement disponible, avec des rendements respectifs de 42 % et de 25 %. [Traduit par la Redaction] Mots-cles : 4-(1-methylpyrrolidin-2-yl)-3-oxobutanoate de methyle, hygrine, intermediaire biosynthetique, alcaloide tropanique, cation N-methylpyrrolinium., Introduction Tropane alkaloids, a family of important natural products found in plants throughout the world, have attracted growing attention becauseoftheir significant biological and pharmacological activity. (1-5) These alkaloids contain complex [...]

Estra-4,9-diene-3,17-dione, an important pharmaceutical intermediate, was synthesized by a three-step sequence from [delta]-lactone 1 in 23.4% overall yield. Reaction of [delta]-lactone 1 and Grignard reagent 2 followed by treatment with Jones reagent resulted in precursor 4. The domino cyclization reaction of 4 with piperidinium acetate gave estra-4,9-diene-3,17-dione. Key words: estra-4,9-diene-3,17-dione, pharmaceutical intermediate, [delta]-lactone, Grignard reaction, Jones reagent, domino cyclization reaction. Nous avons synthétisé l'estra-4,9-diène-3,17-dione, un intermédiaire pharmaceutique d'importance, en trois étapes séquentielles à partir de la [delta]-lactone 1 dans un rendement global de 23,4 %. La réaction entre la [delta]-lactone 1 et le réactif de Grignard 2, suivie d'un traitement par le réactif de Jones a produit le précurseur 4. La réaction de cyclisation domino de l'intermédiaire 4 avec l'acétate de pipéridinium a donné l'estra-4,9-diène-3,17-dione. [Traduit par la Rédaction] Mots-clés : estra-4,9-diène-3,17-dione, intermédiaire pharmaceutique, [delta]-lactone, réaction de Grignard, réactif de Jones, réaction de cyclisation domino., Introduction Estra-4,9-diene-3,17-dione is an important pharmaceutical intermediate in the synthesis of steroids with progestagenic activity (1-3) such as Mifepristone (4-7) and Ulipristal Acetate (8-11) (Fig. 1). Thus, a convenient construction [...]

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