| Revista: | Journal of the Brazilian Chemical Society |
| Base de datos: | PERIÓDICA |
| Número de sistema: | 000311114 |
| ISSN: | 0103-5053 |
| Autors: | Pereira, Leticia O.R1 Cunha, Anna C2 Souza, Maria Cecilia B.V. de Ferreira, Vitor F |
| Institucions: | 1Universidade Federal Fluminense, Instituto de Quimica, Niteroi, Rio de Janeiro. Brasil 2Universidade Federal do Rio de Janeiro, Nucleo de Pesquisa de Produtos Naturais, Rio de Janeiro. Brasil |
| Any: | 2002 |
| Període: | Jun |
| Volum: | 13 |
| Número: | 3 |
| Paginació: | 368-374 |
| País: | Brasil |
| Idioma: | Inglés |
| Tipo de documento: | Artículo |
| Enfoque: | Experimental, aplicado |
| Resumen en inglés | The synthesis of reverse pyrrole ribonucleosides methyl 5-C-(4-acetyl-5-methyl-pyrrol-1-yl)-2,3-O-isopropylidene-5-deoxy- beta-D-ribofuranoside (10), methyl 5-C-(4-ethoxycarbonyl-5-methyl-pyrrol-1-yl)-2,3-O-isopropylidene-5-deoxy- beta-D-ribofuranoside (11), methyl 5-C-(4-acetyl-5-methyl-pyrrol-1-yl)-5-deoxy-beta-D-ribofuranoside (12), methyl 5-C-(4-ethoxycarbonyl-5-methyl-pyrrol-1-yl)-5-deoxy- beta-D-ribofuranoside (13), methyl 5-deoxy-5-C-(3'-formyl-4'-hydroxypropyl-pyrrol-1'-yl)-2,3-O-isopropylidene- beta-D-ribofuranoside (16) and methyl 5-deoxy-5-C-(3'-formyl-pyrrol-1'-yl)-2,3-O-isopropylidene- beta-D-ribofuranoside (18) are described starting from readily available methyl 5-amino-5-deoxy-2,3-O-isopropylidene-beta-D-ribofuranoside (9). The synthetic strategy for the construction of the heterocyclic ring was based on the nucleophilic attack of (9) to 4-acetyl-2-n-butoxy-5-methyl-4,5-dihydrofuran (4), 4-carbetoxy-2-n-butoxy-5-methyl-4,5-dihydrofuran (5), 4-formyl-2-n-butoxy-4,5-dihydrofuran (6) and 4-formyl-1-methyl dioxabyciclo[3.3.0]oct-3-en (8, in situ). The later compounds were obtained from reaction between 3-diazo-2,4-pentadione (1), ethyl 2-diazoacetoacetate (2) or diazomalonaldehyde (3) and enol ethers using dirhodium tetraacetate as a catalyst |
| Resumen en portugués | Neste trabalho estão descritas as sínteses dos ribonucleosídeos pirrólicos reversos 5-C-(4-acetil-5-metil-pirrol-1-il)-2,3-O-isopropilideno-5-desoxi- beta-D-ribofuranosídeo de metila (10), 5-C-(4-etoxicarbonil-5-metil-pirrol-1-il)-2,3-O-isopropilideno-5-desoxi- beta-D-ribofuranosídeo de metila (11), 5-C-(4-acetil-5-metil-pirrol-1-il)-5-desoxi-beta-D-ribofuranosídeo de metila (12), 5-C-(4-etoxicarbonil-5-metil-pirrol-1-il)-5-desoxi- beta-D-ribofuranosídeo de metila (13), 5-desoxi-5-C-(3'-formil-4'-hidroxipropil-pirrol-1'-il)-2,3-O-isopropilideno- beta-D-ribofuranosídeo de metila (16) e 5-desoxi-5-C-(3'-formil-pirrol-1'-il)-2,3-O-isopropilideno- beta-D-ribofuranosídeo de metila (18) a partir do 5-amino-5-desoxi-2,3-O-isopropilideno-beta-D-ribofuranosídeo de metila (9), matéria-prima de fácil preparação. A estratégia sintética para a construção do anel heterocíclico baseou-se no ataque nucleofílico da amina 9 aos diidrofuranos: 4-acetil-2-n-butoxi-5-metil-4,5-diidrofurano (4), 4-carbetoxi-2-n-butoxi-5-metil-4,5-diidrofurano (5), 4-formil-2-n-butoxi-4,5-diidrofurano (6) e 4-formil-1-metil dioxabiciclo[3.3.0]oct-3-eno (8, in situ), obtidos através da reação dos diazo compostos 3-diazo-2,4-pentadiona (1), 2-diazoacetoacetato de etila (2) e diazomalonaldeído (3) com enol-éteres, sob catálise de tetraacetato de di-ródio |
| Disciplines | Química |
| Paraules clau: | Química orgánica, Síntesis orgánica, Pirrol nucleósidos, Rutas de síntesis |
| Keyword: | Chemistry, Organic chemistry, Organic synthesis, Pyrrole nucleosides, Synthetic routes |
| Text complet: | Texto completo (Ver HTML) |
