Abstract
The title compound, C19H29O4, 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 pyrrolidin-1-ylmethyl group as a substituent. The five-membered lactone ring has an envelope conformation, whereas the ten-membered and pyrrolidine rings display approximate chair–chair and twisted conformations, respectively. The dihedral angle between the ten-membered ring and the lactone ring is 18.01 (19)°. An intramolecular O—H⋯N hydrogen bond occurs. The crystal structure is stabilized by weak intermolecular C—H⋯O hydrogen-bonding interactions.
Highlights
The title compound, C19H29O4, was synthesized from 9hydroxyparthenolide (9-hydroxy-4,8-dimethyl-12-methylen3,14-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 natural sesquiterpene lactone 9α-hydroxypartenolide is the main constituent of the chloroform extract of the aerial parts of Anvillea radiata (El Hassany et al, 2004) and of Anvillea garcini (Abdel Sattar et al, 1996)
Symmetry codes: (i) x+1/2, −y+5/2, −z; (ii) x−1/2, −y+3/2, −z
Summary
Avignant,b Abdelghani Oudahmane,b Mohamed Akssirac and Moha Berrahoa a Laboratoire de Chimie Biomoleculaire, Substances Naturelles et Réactivité, URAC16, Faculté des Sciences Semlalia, BP 2390 Bd My Abdellah, 40000. Laboratoire de Chimie Bioorganique et Analytique, URAC 22, BP 146, FSTM, Université Hassan II, Mohammedia–Casablanca 20810 Mohammedia, Morocco. R factor = 0.045; wR factor = 0.121; data-to-parameter ratio = 9.5. The molecule is built up from two fused fiveand ten-membered rings with the pyrrolidin-1-ylmethyl group as a substituent. The five-membered lactone ring has an envelope conformation, whereas the ten-membered and pyrrolidine rings display approximate chair–chair and twisted conformations, respectively. The dihedral angle between the ten-membered ring and the lactone ring is 18.01 (19). An intramolecular O—H N hydrogen bond occurs. The crystal structure is stabilized by weak intermolecular C—H O hydrogen-bonding interactions
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