Cargando…
Redetermination and absolute configuration of (+)-7-epiclusianone
The absolute configuration of 3-benzoyl-4-hydroxy-6,6-dimethyl-1,5,7-tris(3-methylbut-2-enyl)bicyclo[3.3.1]non-3-ene-2,9-dione, C(33)H(42)O(4), isolated from Hypericum hypericoides, has been determined. The previous study [Xiao et al. (2007 ▶). J. Nat. Prod. 70, 1779–1782] gave only the establi...
Autores principales: | , , , , , |
---|---|
Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
International Union of Crystallography
2012
|
Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3515307/ https://www.ncbi.nlm.nih.gov/pubmed/23284527 http://dx.doi.org/10.1107/S1600536812043784 |
_version_ | 1782252156754067456 |
---|---|
author | Christian, Omar E. Fronczek, Frank R. Ky, Khoa Pradhan, Shreedu Manandhar, Anjela Richmond, Cecilia |
author_facet | Christian, Omar E. Fronczek, Frank R. Ky, Khoa Pradhan, Shreedu Manandhar, Anjela Richmond, Cecilia |
author_sort | Christian, Omar E. |
collection | PubMed |
description | The absolute configuration of 3-benzoyl-4-hydroxy-6,6-dimethyl-1,5,7-tris(3-methylbut-2-enyl)bicyclo[3.3.1]non-3-ene-2,9-dione, C(33)H(42)O(4), isolated from Hypericum hypericoides, has been determined. The previous study [Xiao et al. (2007 ▶). J. Nat. Prod. 70, 1779–1782] gave only the established relative configuration. The three stereogenic centers are now established as 1R, 5R and 7S on the basis of the refinement of the Flack absolute structure parameter against Cu Kα data and correspond to a specific rotation of [α](D) (20) = +66°. The enol–hydroxy group forms an intramolecular O—H⋯O hydrogen bond to close an S(6) ring. |
format | Online Article Text |
id | pubmed-3515307 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2012 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-35153072013-01-02 Redetermination and absolute configuration of (+)-7-epiclusianone Christian, Omar E. Fronczek, Frank R. Ky, Khoa Pradhan, Shreedu Manandhar, Anjela Richmond, Cecilia Acta Crystallogr Sect E Struct Rep Online Organic Papers The absolute configuration of 3-benzoyl-4-hydroxy-6,6-dimethyl-1,5,7-tris(3-methylbut-2-enyl)bicyclo[3.3.1]non-3-ene-2,9-dione, C(33)H(42)O(4), isolated from Hypericum hypericoides, has been determined. The previous study [Xiao et al. (2007 ▶). J. Nat. Prod. 70, 1779–1782] gave only the established relative configuration. The three stereogenic centers are now established as 1R, 5R and 7S on the basis of the refinement of the Flack absolute structure parameter against Cu Kα data and correspond to a specific rotation of [α](D) (20) = +66°. The enol–hydroxy group forms an intramolecular O—H⋯O hydrogen bond to close an S(6) ring. International Union of Crystallography 2012-10-27 /pmc/articles/PMC3515307/ /pubmed/23284527 http://dx.doi.org/10.1107/S1600536812043784 Text en © Christian et al. 2012 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 | Organic Papers Christian, Omar E. Fronczek, Frank R. Ky, Khoa Pradhan, Shreedu Manandhar, Anjela Richmond, Cecilia Redetermination and absolute configuration of (+)-7-epiclusianone |
title | Redetermination and absolute configuration of (+)-7-epiclusianone |
title_full | Redetermination and absolute configuration of (+)-7-epiclusianone |
title_fullStr | Redetermination and absolute configuration of (+)-7-epiclusianone |
title_full_unstemmed | Redetermination and absolute configuration of (+)-7-epiclusianone |
title_short | Redetermination and absolute configuration of (+)-7-epiclusianone |
title_sort | redetermination and absolute configuration of (+)-7-epiclusianone |
topic | Organic Papers |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3515307/ https://www.ncbi.nlm.nih.gov/pubmed/23284527 http://dx.doi.org/10.1107/S1600536812043784 |
work_keys_str_mv | AT christianomare redeterminationandabsoluteconfigurationof7epiclusianone AT fronczekfrankr redeterminationandabsoluteconfigurationof7epiclusianone AT kykhoa redeterminationandabsoluteconfigurationof7epiclusianone AT pradhanshreedu redeterminationandabsoluteconfigurationof7epiclusianone AT manandharanjela redeterminationandabsoluteconfigurationof7epiclusianone AT richmondcecilia redeterminationandabsoluteconfigurationof7epiclusianone |