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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...

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Detalles Bibliográficos
Autores principales: Stierle, Andrea, Stierle, Donald, Decato, Daniel
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2015
Materias:
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].
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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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