Abstract
The title compound, C15H21ClO4, 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 fused five- and ten-membered rings. The five-membered lactone ring has an envelope conformation with the flap atom, C(H)-C-C(H), displaced by 0.2325 (15) Å from the mean plane through the remaining four atoms, whereas the ten-membered ring displays an approximate chair–chair conformation. The dihedral angle between the two rings is 66.4 (2)°. In the crystal, molecules are linked into chains propagating along the a axis by O—H⋯O hydrogen bonds.
Highlights
The title compound, C15H21ClO4, 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
Molecules are linked into chains propagating along the a axis by O—H O hydrogen bonds
We have treated 9α-hydroxyparthenolide with 5% of titanium tetrachloride (TiCl4)and obtained (1S, 2R, 3R, 8R, 10S)-3-chloro-2,8- dihydroxy-3,7-dimethyl-11-methylene-13-oxabicyclo[8.3.0]tridec-6-en-12-one with a yield of 52%
Summary
Moha Berrahoa a Laboratoire de Chimie Biomoleculaire, Substances Naturelles et Réactivité, URAC16, Faculté des Sciences Semlalia, BP 2390 Bd My Abdellah, 40000. Morocco, bLaboratoire de Chimie de Coordination, 205 route de Narbonne, 31077 Toulouse Cedex 04, France, and cLaboratoire de Chimie. BP 146, FSTM, Université Hassan II, Mohammedia–Casablanca 20810 Mohammedia, Morocco. R factor = 0.027; wR factor = 0.070; data-to-parameter ratio = 16.5. The title compound, C15H21ClO4, 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 molecule is built up from fused five- and ten-membered rings. The dihedral angle between the two rings is 66.4 (2). Molecules are linked into chains propagating along the a axis by O—H O hydrogen bonds
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