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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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Detalles Bibliográficos
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
Descripción
Sumario: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.