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Crystal structure and absolute configuration of preaustinoid A1
The absolute structure of the title compound preaustinoid A1 [systematic name: (5aR,7aS,8R,10S,12R,13aR,13bS)-methyl 10-hydroxy-5,5,7a,10,12,13b-hexamethyl-14-methylene-3,9,11-trioxohexadecahydro-8,12-methanocycloocta[3,4]benzo[1,2-c]oxepine-8-carboxylate], C(26)H(36)O(7), has been determin...
Autores principales: | , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
International Union of Crystallography
2015
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Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4571416/ https://www.ncbi.nlm.nih.gov/pubmed/26396816 http://dx.doi.org/10.1107/S2056989015013614 |
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author | Stierle, Andrea Stierle, Donald Decato, Daniel |
author_facet | Stierle, Andrea Stierle, Donald Decato, Daniel |
author_sort | Stierle, Andrea |
collection | PubMed |
description | The absolute structure of the title compound preaustinoid A1 [systematic name: (5aR,7aS,8R,10S,12R,13aR,13bS)-methyl 10-hydroxy-5,5,7a,10,12,13b-hexamethyl-14-methylene-3,9,11-trioxohexadecahydro-8,12-methanocycloocta[3,4]benzo[1,2-c]oxepine-8-carboxylate], C(26)H(36)O(7), has been determined by resonant scattering using Cu Kα radiation [Flack parameter = 0.07 (15)]. The structure is consistent with that reported previously [Stierle et al. (2011). J. Nat. Prod. 74, 2272–2277], determined by detailed analysis of MS and NMR data. The molecule consists of a fused four-ring arrangement. The seven-membered oxepan-2-one ring has a chair conformation, as do the central cyclohexane rings, while the outer cyclohexa-1,3-dione ring has a boat conformation. In the crystal, molecules are linked via O—H⋯O hydrogen bonds, forming helical chains propagating along [100]. |
format | Online Article Text |
id | pubmed-4571416 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2015 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-45714162015-09-22 Crystal structure and absolute configuration of preaustinoid A1 Stierle, Andrea Stierle, Donald Decato, Daniel Acta Crystallogr E Crystallogr Commun Data Reports The absolute structure of the title compound preaustinoid A1 [systematic name: (5aR,7aS,8R,10S,12R,13aR,13bS)-methyl 10-hydroxy-5,5,7a,10,12,13b-hexamethyl-14-methylene-3,9,11-trioxohexadecahydro-8,12-methanocycloocta[3,4]benzo[1,2-c]oxepine-8-carboxylate], C(26)H(36)O(7), has been determined by resonant scattering using Cu Kα radiation [Flack parameter = 0.07 (15)]. The structure is consistent with that reported previously [Stierle et al. (2011). J. Nat. Prod. 74, 2272–2277], determined by detailed analysis of MS and NMR data. The molecule consists of a fused four-ring arrangement. The seven-membered oxepan-2-one ring has a chair conformation, as do the central cyclohexane rings, while the outer cyclohexa-1,3-dione ring has a boat conformation. In the crystal, molecules are linked via O—H⋯O hydrogen bonds, forming helical chains propagating along [100]. International Union of Crystallography 2015-07-22 /pmc/articles/PMC4571416/ /pubmed/26396816 http://dx.doi.org/10.1107/S2056989015013614 Text en © Stierle et al. 2015 http://creativecommons.org/licenses/by/2.0/uk/ This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited. |
spellingShingle | Data Reports Stierle, Andrea Stierle, Donald Decato, Daniel Crystal structure and absolute configuration of preaustinoid A1 |
title | Crystal structure and absolute configuration of preaustinoid A1 |
title_full | Crystal structure and absolute configuration of preaustinoid A1 |
title_fullStr | Crystal structure and absolute configuration of preaustinoid A1 |
title_full_unstemmed | Crystal structure and absolute configuration of preaustinoid A1 |
title_short | Crystal structure and absolute configuration of preaustinoid A1 |
title_sort | crystal structure and absolute configuration of preaustinoid a1 |
topic | Data Reports |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4571416/ https://www.ncbi.nlm.nih.gov/pubmed/26396816 http://dx.doi.org/10.1107/S2056989015013614 |
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