12-Anilinomethyl-9α-hy­droxy-4,8-dimethyl-3,14-dioxatricyclo­[9.3.0.02,4]tetra­dec-7-en-13-one

The title compound, C21H27NO4, was synthesized from 9α-hy­droxy­parthenolide, which was isolated from the chloro­form extract of the aerial parts of Anvillea radiata. The asymmetric unit contains two independent mol­ecules. In each, the ten-membered ring displays an approximative chair-chair conformation. Each of the five-membered rings adopts a flattened envelope conformation, the C(H)—C—C(H) atoms representing the flap lie out of the mean plane through the remaining four atoms by 0.443 (2) and 0.553 (2) Å. The dihedral angle between the least-squares planes through the ten- and five-membered rings in the two mol­ecules are similar [22.54 (17) and 23.39 (14)°]. In the crystal, mol­ecules are linked by O—H⋯O, O—H⋯N and N—H⋯O hydrogen bonds

5,9-Dihy­droxy-9-methyl-3,6-dimethyl­ene-3a,4,5,6,6a,7,8,9,9a,9b-deca­hydro­azuleno[4,5-b]furan-2(3H)-one

The title compound, C15H20O4, was synthesized from 9α-hy­droxy­parthenolide (9α-hy­droxy-4,8-dimethyl-12-methyl­ene-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 seven-membered ring has a chair conformation, while the five-membered rings display twisted conformations. The dihedral angle between the seven-membered ring and the lactone ring is 21.69 (10)°. In the crystal, mol­ecules are linked into chains propagating along the c axis by inter­molecular O—H⋯O hydrogen bonds; an intra­molecular O—H⋯O link also occurs

10α-Hy­droxy-4,9-dimethyl-13-(morph­o­lin-4-ylmeth­yl)-3,8,15-trioxatetra­cyclo­[10.3.0.02,4.07,9]penta­decan-14-one

The title compound, C19H29NO6, was synthesized from 9α-hy­droxy­parthenolide (9α-hy­droxy-4,8-dimethyl-12-methyl­ene-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 contains a fused five- and ten-membered ring system. The ten-membered ring adopts an approximate chair–chair conformation, while the five-membered ring is in an envelope conformation, with the C atom closest to the hy­droxy group forming the flap. In the crystal, weak C—H⋯O hydrogen bonds connect the mol­ecules into layers parallel to (001). An intra­molecular O—H⋯N hydrogen bond is also present

10α-Hy­droxy-4,9-dimethyl-13-[(pyrrol­idin-1-yl)meth­yl]-3,8,15-trioxatetra­cyclo­[10.3.0.02,4.07,9]penta­decan-14-one

The title compound, C19H29NO5, was synthesized from 9α-hy­droxy­parthenolide (9α-hy­droxy-4,8-dimethyl-12-methyl­ene-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-4-yl)methyl group as a substituent. The two five-membered ring display the same envelope conformations, whereas the ten-membered ring adopts an approximate chair–chair conformation. The dihedral angle between the ten-membered ring and the lactone ring is 21.81 (9)°. An intra­molecular O—H⋯N hydrogen bond stabilizes the mol­ecular conformation. In the crystal, inter­molecular C—H⋯O inter­actions link the mol­ecules into chains parallel to the c axis

10α-Hy­droxy-13-{[4-(4-meth­oxy­phen­yl)piperazin-1-yl]meth­yl}-4,9-dimethyl-3,8,15-trioxatetra­cyclo­[10.3.0.02,4.07,9]penta­decan-14-one

The title compound, C26H36N2O6, 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 two additional ep­oxy ring systems and a meth­oxy­phenyl­piperazine group as a substituent. The ten-membered ring adopts an approximate chair–chair conformation, while the piperazine ring displays a chair conformation and the five-membered ring shows an envelope conformation with the C atom closest to the hy­droxy group forming the flap. The mol­ecular conformation is determined by an O—H⋯N hydrogen bond between the hy­droxy group and a piperazine N atom. The crystal structure is built up by weak C—H⋯O inter­actions

12-{[4-(2-Fluoro­phen­yl)piperazin-1-yl]­meth­yl}-9α-hy­droxy-4,8-dimethyl-3,14-dioxatricyclo­[9.3.0.02,4]tetra­dec-7-en-13-one

The title compound, C25H33FN2O4, was synthesized from 9α-hy­droxy­parthenolide (9α-hy­droxy-4,8-dimethyl-12-methyl­ene-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 asymmetric unit contains two independent mol­ecules. In each mol­ecule, the ten-membered ring displays an approximative chair–chair conformation. Each of the piperazine rings adopts a perfect chair conformation, while both lactone rings show an envelope conformation, one with the C atom bearing the piperazin-1-ylmethyl group as the flap, the other with the junction C atom not attached to the ring O atom as the flap. The dihedral angles between the least-squares planes through the ten- and five-membered rings in the two mol­ecules are similar [19.1 (3) and 16.2 (3)°]. An intra­molecular O—H⋯N hydrogen bond stabilizes the mol­ecular conformation. The crystal packing is stabilized by C—H⋯O hydrogen bonds

9α-Acet­oxy-1β,10α-ep­oxy­parthenolide

The title compound, C17H22O6, was semi-synthesized from 9-hy­droxy­arthenolide, which was isolated from the chloro­form extract of the aerial parts of Anvillea radiata. The mol­ecule contains fused five- and ten-membered rings: the five-membered lactone ring has a twisted conformation, whereas the ten-membered ring displays an approximate chair–chair conformation. The dihedral angle between the rings is 24.76 (9)°

10α-Hy­droxy-4,9-dimethyl-13-[(4-phenyl­piperazin-1-yl)meth­yl]-3,8,15-trioxatetra­cyclo­[10.3.0.02,4.07,9]tetra­decan-14-one

The title compound, C25H34N2O5, was synthesized from 9α-hy­droxy­parthenolide (9α-hy­droxy-4,8-dimethyl-12-methyl­ene-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 contains a fused five- and ten-membered ring system. The ten-membered ring adopts an approximate chair–chair conformation, while the five-membered ring is in an envelope conformation, with the C atom closest to the hy­droxy group forming the flap. The piperazine ring is in a chair conformation. In the crystal, O—H⋯O hydrogen bonds connect mol­ecules into chains along [100]. Weak inter­molecular C—H⋯O hydrogen bonds are also present

10α-Hy­droxy-4,9-dimethyl-13-(pipyridin-1-ylmethyl)-3,8,15-trioxatetra­cyclo­[10.3.0.02,4.07,9]tetra­decan-14-one

The title compound, C20H31NO5, 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- and five-membered rings display chair and envelope conformations, respectively. The dihedral angle between the mean planes of the ten-membered ring and the lactone ring is 20.8 (3)°. An intra­molecular O—H⋯N hydrogen-bond occurs. The crystal structure is stabilized by weak inter­molecular C—H⋯O hydrogen bonds

(1S,2R,3R,6R,7S,8R,10S,11S)-13-{[4-(4-Chloro­phen­yl)piperazin-1-yl]meth­yl}-10-hy­droxy-4,9-dimethyl-3,8,15-trioxatetra­cyclo­[10.3.0.02,4.07,9]penta­decan-14-one

The title compound, C25H33ClN2O5, was synthesized from 9α-hy­droxy­parthenolide (9α-hy­droxy-4,8-dimethyl-12-methyl­ene-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 with two additional ep­oxy ring systems and a chloro­phenyl­piperazine group as a substituent. The ten-membered ring adopts an approximate chair–chair conformation, while the piperazine ring displays a chair conformation and the five-membered ring shows an envelope conformation with the C atom closest to the hy­droxy group forming the flap. The mol­ecular conformation is stabilized by an intra­molecular O—H⋯N hydrogen bond between the hy­droxy group and a piperazine N atom. The crystal structure is stabilized by weak C—H⋯O inter­actions