Preparation and Characterization of Rosmarinecine Derivatives
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| Format: | Artículo científico |
| Language: | en |
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Sociedad Química de México
2006
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| _version_ | 1876459913731899392 |
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| author | David Aarón Nieto |
| author_facet | David Aarón Nieto |
| contents | Preparation and Characterization of Rosmarinecine Derivatives David Aarón Nieto Teresa Mancilla Percino Multidisciplinaria (Ciencias Naturales y Exactas) Alkaloids Spectroscopy Pyrrolizidine Hydroxypyrrolizidine Rosmarinecine derivatives This work describes the synthesis of 8-tert-butyldimethylsilyloxy-(3), 2,8-bis(tert-butyldimethylsilyloxy)- (4) 2-mesyloxy-8-tert-butyldimethylsilyloxy- (5), and 2-tosyloxyrosmarinecine(6) from selective protection of the different hydroxylgroups of rosmarinecine 2, which was obtained by hydrolysis of rosmarinine1. The rosmarinine 1 naturally occuring was isolated ingood yields (0.66%) from Senecio callosus. The chemoselectivity ofthe silylation of the hydroxyl groups at position C-2 and C-8 of 2 wascontrolled by the time of the reaction, which exhibited a higher reactivityfor primary hydroxyl than secondary hydroxyl group, as well asthe stereochemistry of the group at 1 position, which is trans and cisto the hydroxyl groups at 2 and 7 positions, respectively, where thesteric efffect of hydroxyl group at 7 position is evidenced and possibleeffect of the solvent. The compounds were characterized by 1H,13C NMR, 1H-1H COSY, HETCOR spectra, infrared and mass spectrometry 2006 artículo científico 1870-249X https://www.redalyc.org/articulo.oa?id=47550404 en http://www.redalyc.org/revista.oa?id=475 Journal of the Mexican Chemical Society application/pdf Sociedad Química de México Journal of the Mexican Chemical Society (México) Num.4 Vol.50 |
| format | Artículo científico |
| id | redalyc_47550404 |
| institution | Redalyc |
| language | en |
| publishDate | 2006 |
| publisher | Sociedad Química de México |
| spellingShingle | Preparation and Characterization of Rosmarinecine Derivatives David Aarón Nieto Multidisciplinaria (Ciencias Naturales y Exactas) Alkaloids Spectroscopy Pyrrolizidine Hydroxypyrrolizidine Rosmarinecine derivatives Preparation and Characterization of Rosmarinecine Derivatives David Aarón Nieto Teresa Mancilla Percino Multidisciplinaria (Ciencias Naturales y Exactas) Alkaloids Spectroscopy Pyrrolizidine Hydroxypyrrolizidine Rosmarinecine derivatives This work describes the synthesis of 8-tert-butyldimethylsilyloxy-(3), 2,8-bis(tert-butyldimethylsilyloxy)- (4) 2-mesyloxy-8-tert-butyldimethylsilyloxy- (5), and 2-tosyloxyrosmarinecine(6) from selective protection of the different hydroxylgroups of rosmarinecine 2, which was obtained by hydrolysis of rosmarinine1. The rosmarinine 1 naturally occuring was isolated ingood yields (0.66%) from Senecio callosus. The chemoselectivity ofthe silylation of the hydroxyl groups at position C-2 and C-8 of 2 wascontrolled by the time of the reaction, which exhibited a higher reactivityfor primary hydroxyl than secondary hydroxyl group, as well asthe stereochemistry of the group at 1 position, which is trans and cisto the hydroxyl groups at 2 and 7 positions, respectively, where thesteric efffect of hydroxyl group at 7 position is evidenced and possibleeffect of the solvent. The compounds were characterized by 1H,13C NMR, 1H-1H COSY, HETCOR spectra, infrared and mass spectrometry 2006 artículo científico 1870-249X https://www.redalyc.org/articulo.oa?id=47550404 en http://www.redalyc.org/revista.oa?id=475 Journal of the Mexican Chemical Society application/pdf Sociedad Química de México Journal of the Mexican Chemical Society (México) Num.4 Vol.50 |
| title | Preparation and Characterization of Rosmarinecine Derivatives |
| topic | Multidisciplinaria (Ciencias Naturales y Exactas) Alkaloids Spectroscopy Pyrrolizidine Hydroxypyrrolizidine Rosmarinecine derivatives |
| url | https://www.redalyc.org/articulo.oa?id=47550404 |