9-Hydroxy-4,8-dimethyl-12-(piperidin-1-ylmethyl)-3,14-dioxatricyclo[9.3.0.02,4]tetradec-7-en-13-one

Abstract

The title compound, C20H31NO4, was synthesized from 9α-hydroxyparthenolide (9α-hydroxy-4,8-dimethyl-12-methylen-3,14-dioxa-tricyclo[9.3.0.02,4]tetradec-7-en-13-one), which was isolated from the chloroform extract of the aerial parts of Anvillea radiata. The molecule is built up from fused five-and ten-membered rings with the pipyridin-1-yl-methyl group as a substituent. The ten-membered ring adopts an approximate chair–chair conformation, while the six-membered ring display a chair conformation and the five-membered ring an envelope conformation with the C(H)–C–C(H) atom at the flap. The dihedral angle between the ten-membered ring and the lactone ring is 21.7 (4)°. The molecular conformation is stabilized by an O—H...N hydrogen bond and the crystal structure is stabilized by weak intermolecular C—H...O interactions.