(Z)-6-Hydroxy-1a,5-dimethyl-8-[(morpholin-4-yl)methyl]-2,3,6,7,7a,8,10a,10b-octahydrooxireno[2′,3′:9,10]cyclodeca[1,2-b]furan-9(1aH)-one

Abstract

The title compound, C19H29NO5, was synthesized from 9α-hydroxyparthenolide (9α-hydroxy-4,8-dimethyl-12-methylen-3,14-dioxatricyclo[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 two fused five- and ten-membered rings with the (morpholin-4-yl)methyl group as a substituent. The five-membered lactone ring has an envelope conformation, whereas the ten-membered and the morpholine rings display approximate chair–chair and chair conformations, respectively. The dihedral angle between the ten-membered ring and the lactone ring is 27.93 (6)°. The crystal structure is stabilized by weak intermolecular C—H...O hydrogen-bond interactions. An intramolecular O—H...N hydrogen bond also occurs.