Accurate stereochemistry for two related 22,26-epiminocholestene derivatives
Regioselective opening of ring E of solasodine under various conditions afforded (25R)-22,26-epiminocholesta-5,22(N)-diene-3�,16�-diyl diacetate (previously known as 3,16-diacetyl pseudosolasodine B), C31H47NO4, or (22S,25R)-16�-hydroxy22,26-epiminocholesta-5-en-3�-yl acetate (a derivative of the na...
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| Format: | Article |
| Language: | English |
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International Union of Crystallography
2008
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| Online Access: | http://eprints.uanl.mx/29661/7/29661.pdf |
| _version_ | 1838551019685937152 |
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| author | Vega Báez, José Luis Sandoval Ramírez, Jesús Meza Reyes, Socorro Montiel Smith, Sara Gómez Calvario, Victor Bernès, Sylvain |
| author_facet | Vega Báez, José Luis Sandoval Ramírez, Jesús Meza Reyes, Socorro Montiel Smith, Sara Gómez Calvario, Victor Bernès, Sylvain |
| author_sort | Vega Báez, José Luis |
| collection | Repositorio Institucional |
| description | Regioselective opening of ring E of solasodine under various conditions afforded (25R)-22,26-epiminocholesta-5,22(N)-diene-3�,16�-diyl diacetate (previously known as 3,16-diacetyl pseudosolasodine B), C31H47NO4, or (22S,25R)-16�-hydroxy22,26-epiminocholesta-5-en-3�-yl acetate (a derivative of the naturally occurring alkaloid oblonginine), C29H47NO3. In both cases, the reactions are carried out with retention of chirality at the C16, C20 and C25 stereogenic centers, which are found to be S, S and R, respectively. Although pseudosolasodine was synthesized 50 years ago, these accurate assignments clarify some controversial points about the actual stereochemistry for these alkaloids. This is of particular importance in the case of oblonginine, since this compound is currently under consideration for the treatment of aphasia arising from apoplexy; the present study defines a diastereoisomerically pure compound for pharmacological studies. |
| format | Article |
| id | eprints-29661 |
| institution | UANL |
| language | English |
| publishDate | 2008 |
| publisher | International Union of Crystallography |
| record_format | eprints |
| spelling | eprints-296612025-07-16T15:22:42Z http://eprints.uanl.mx/29661/ Accurate stereochemistry for two related 22,26-epiminocholestene derivatives Vega Báez, José Luis Sandoval Ramírez, Jesús Meza Reyes, Socorro Montiel Smith, Sara Gómez Calvario, Victor Bernès, Sylvain QD Química Regioselective opening of ring E of solasodine under various conditions afforded (25R)-22,26-epiminocholesta-5,22(N)-diene-3�,16�-diyl diacetate (previously known as 3,16-diacetyl pseudosolasodine B), C31H47NO4, or (22S,25R)-16�-hydroxy22,26-epiminocholesta-5-en-3�-yl acetate (a derivative of the naturally occurring alkaloid oblonginine), C29H47NO3. In both cases, the reactions are carried out with retention of chirality at the C16, C20 and C25 stereogenic centers, which are found to be S, S and R, respectively. Although pseudosolasodine was synthesized 50 years ago, these accurate assignments clarify some controversial points about the actual stereochemistry for these alkaloids. This is of particular importance in the case of oblonginine, since this compound is currently under consideration for the treatment of aphasia arising from apoplexy; the present study defines a diastereoisomerically pure compound for pharmacological studies. International Union of Crystallography 2008-03-15 Article PeerReviewed text en cc_by_nc_nd http://eprints.uanl.mx/29661/7/29661.pdf http://eprints.uanl.mx/29661/7.haspreviewThumbnailVersion/29661.pdf Vega Báez, José Luis y Sandoval Ramírez, Jesús y Meza Reyes, Socorro y Montiel Smith, Sara y Gómez Calvario, Victor y Bernès, Sylvain (2008) Accurate stereochemistry for two related 22,26-epiminocholestene derivatives. Acta Crystallographica Section C Crystal Structure Communications, 64 (4). o214-o216. ISSN 0108-2701 doi:10.1107/S0108270108005763 |
| spellingShingle | QD Química Vega Báez, José Luis Sandoval Ramírez, Jesús Meza Reyes, Socorro Montiel Smith, Sara Gómez Calvario, Victor Bernès, Sylvain Accurate stereochemistry for two related 22,26-epiminocholestene derivatives |
| thumbnail | https://rediab.uanl.mx/themes/sandal5/images/online.png |
| title | Accurate stereochemistry for two related 22,26-epiminocholestene derivatives |
| title_full | Accurate stereochemistry for two related 22,26-epiminocholestene derivatives |
| title_fullStr | Accurate stereochemistry for two related 22,26-epiminocholestene derivatives |
| title_full_unstemmed | Accurate stereochemistry for two related 22,26-epiminocholestene derivatives |
| title_short | Accurate stereochemistry for two related 22,26-epiminocholestene derivatives |
| title_sort | accurate stereochemistry for two related 22 26 epiminocholestene derivatives |
| topic | QD Química |
| url | http://eprints.uanl.mx/29661/7/29661.pdf |
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