Date Published: February 01, 2012
Publisher: International Union of Crystallography
Author(s): Karren D. Beattie, Mohan M. Bhadbhade, Donald C. Craig, David N. Leach.
The title compound, C20H28O3, was isolated during our investigation into the chemical composition and pharmacological activity of Centipeda cunninghamii (DC.) A. Braun & Asch. (Asteraceae). The enantiopure 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 molecule makes one intra- and one intermolecular O—H⋯O hydrogen bond in the crystal lattice, forming hydrogen-bonded chains along . The absolute configuration of the compound was assigned on the basis of optical rotation measurements.
For the characterization of related kaurane diterpenes, see: Reynolds et al. (1991 ▶); Piozzi et al. (1972 ▶). For literature on the occurrence of the 3S isomer of the title compound isolated from Ichthyothere terminalis and Pseudognaphalium cheiranthifolium, see: Bohlmann et al. (1982 ▶); Mendoza & Urzúa (1998 ▶). For the antibacterial activity of the 3S isomer, see: Mendoza et al. (1997 ▶). For phytopharmacological aspects of Centipeda cunninghamii, see: Campbell (1973 ▶); Cribb (1988 ▶); D’Amelio & Mirhom, (1998 ▶); Maiden (1975 ▶); Webb (1948 ▶). For optical rotation data of related compounds, see: Bohlmann et al. (1982 ▶); Brieskorn & Pöhlmann (1968 ▶); Reynolds et al. (1991 ▶).