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

Acta Crystallogr Sect E Struct Rep Online. 2012 Nov 1;68(Pt 11):o3222-3. doi: 10.1107/S1600536812043784. Epub 2012 Oct 27.

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.