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. 2012 Nov 1;68(Pt 11):o3222-3.
doi: 10.1107/S1600536812043784. Epub 2012 Oct 27.

Redetermination and absolute configuration of (+)-7-epiclusianone

Omar E Christian  1 , Frank R Fronczek, Khoa Ky, Shreedu Pradhan, Anjela Manandhar, Cecilia Richmond
Affiliations

Redetermination and absolute configuration of (+)-7-epiclusianone

Omar E Christian et al. Acta Crystallogr Sect E Struct Rep Online. .

Abstract

The absolute configuration of 3-benzoyl-4-hy-droxy-6,6-dimethyl-1,5,7-tris-(3-methyl-but-2-en-yl)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-hy-droxy group forms an intra-molecular O-H⋯O hydrogen bond to close an S(6) ring.

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Figures

Fig. 1.
Fig. 1.
Ellipsoids at the 50% level, with H atoms having arbitrary radius.
Fig. 2.
Fig. 2.
View of the molecule showing the intramolecular hydrogen bond; 50% ellipsoids
See this image and copyright information in PMC

References

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