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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-3β,16β-diyl diacetate (previously known as 3,16-diacetyl pseudosolasodine B), C(31)H(47)NO(4), or (22S,25R)-16β-hydroxy-22,26-epiminocholesta-5-en-3β-yl acetate (a derivativ...
Autores principales: | , , , , , |
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Formato: | Texto |
Lenguaje: | English |
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International Union of Crystallography
2008
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Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2467522/ https://www.ncbi.nlm.nih.gov/pubmed/18391392 http://dx.doi.org/10.1107/S0108270108005763 |
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author | Vega-Baez, José Luis Sandoval-Ramírez, Jesús Meza-Reyes, Socorro Montiel-Smith, Sara Gómez-Calvario, Victor Bernès, Sylvain |
author_facet | Vega-Baez, José Luis Sandoval-Ramírez, Jesús Meza-Reyes, Socorro Montiel-Smith, Sara Gómez-Calvario, Victor Bernès, Sylvain |
author_sort | Vega-Baez, José Luis |
collection | PubMed |
description | Regioselective opening of ring E of solasodine under various conditions afforded (25R)-22,26-epiminocholesta-5,22(N)-diene-3β,16β-diyl diacetate (previously known as 3,16-diacetyl pseudosolasodine B), C(31)H(47)NO(4), or (22S,25R)-16β-hydroxy-22,26-epiminocholesta-5-en-3β-yl acetate (a derivative of the naturally occurring alkaloid oblonginine), C(29)H(47)NO(3). 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 | Text |
id | pubmed-2467522 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2008 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-24675222009-03-05 Accurate stereochemistry for two related 22,26-epiminocholestene derivatives Vega-Baez, José Luis Sandoval-Ramírez, Jesús Meza-Reyes, Socorro Montiel-Smith, Sara Gómez-Calvario, Victor Bernès, Sylvain Acta Crystallogr C Organic Compounds Regioselective opening of ring E of solasodine under various conditions afforded (25R)-22,26-epiminocholesta-5,22(N)-diene-3β,16β-diyl diacetate (previously known as 3,16-diacetyl pseudosolasodine B), C(31)H(47)NO(4), or (22S,25R)-16β-hydroxy-22,26-epiminocholesta-5-en-3β-yl acetate (a derivative of the naturally occurring alkaloid oblonginine), C(29)H(47)NO(3). 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 2008-04-15 2008-03-15 /pmc/articles/PMC2467522/ /pubmed/18391392 http://dx.doi.org/10.1107/S0108270108005763 Text en © International Union of Crystallography 2008 http://journals.iucr.org/services/termsofuse.html This is an open-access article distributed under the terms described at http://journals.iucr.org/services/termsofuse.html. |
spellingShingle | Organic Compounds Vega-Baez, 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 |
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 | Organic Compounds |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2467522/ https://www.ncbi.nlm.nih.gov/pubmed/18391392 http://dx.doi.org/10.1107/S0108270108005763 |
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