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. 2012 Feb 1;68(Pt 2):o526-7.
doi: 10.1107/S1600536812002206. Epub 2012 Jan 25.

(3R,4S,5S,8S,10R,13R)-3-Hy-droxy-kaura-9(11),16-dien-18-oic acid

Karren D Beattie, Mohan M Bhadbhade, Donald C Craig, David N Leach

(3R,4S,5S,8S,10R,13R)-3-Hy-droxy-kaura-9(11),16-dien-18-oic acid

Karren D Beattie et al. Acta Crystallogr Sect E Struct Rep Online. .

Abstract

The title compound, C(20)H(28)O(3), was isolated during our investigation into the chemical composition and pharmacological activity of Centipeda cunninghamii (DC.) A. Braun & Asch. (Asteraceae). The enanti-opure compound, a diterpene with a carbon skeleton, is composed of three six- and one five-membered rings in chair, twist-boat, half-chair and envelope conformations, respectively. Each mol-ecule makes one intra- and one inter-molecular O-H⋯O hydrogen bond in the crystal lattice, forming hydrogen-bonded chains along [010]. The absolute configuration of the compound was assigned on the basis of optical rotation measurements.

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Figures

Fig. 1.
Fig. 1.
View of (I) with atom numbering scheme. Displacement ellipsoids for non-H atoms are drawn at the 40% probability level.
Fig. 2.
Fig. 2.
Packing diagram of (I) viewed down the a axis depicting intra and inter molecular O—H···O hydrogen bonding.
See this image and copyright information in PMC

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