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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...

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Autores principales: Christian, Omar E., Fronczek, Frank R., Ky, Khoa, Pradhan, Shreedu, Manandhar, Anjela, Richmond, Cecilia
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
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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.
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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
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