(1S,2R,3R,8R,10S)-3-Chloro-2,8-dihydroxy-3,7-dimethyl-11-methylidene-13-oxabicyclo[8.3.0]tridec-6-en-12-one
نویسندگان
چکیده
The title compound, C(15)H(21)ClO(4), was synthesized from 9α-hy-droxy-parthenolide (9α-hy-droxy-4,8-dimethyl-12-methylen-3,14-dioxatricyclo-[9.3.0.0(2,4)]tetra-dec-7-en-13-one), which was isolated from the chloro-form extract of the aerial parts of Anvillea radiata. The mol-ecule 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, mol-ecules are linked into chains propagating along the a axis by O-H⋯O hydrogen bonds.
منابع مشابه
(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, C(25)H(33)ClN(2)O(5), was synthesized from 9α-hy-droxy-parthenolide (9α-hy-droxy-4,8-dimethyl-12-methyl-ene-3,14-dioxatricyclo-[9.3.0.0(2,4)]tetra-dec-7-en-13-one), which was isolated from the chloro-form extract of the aerial parts of Anvillea radiata. The mol-ecule is built up from fused five- and ten-membered rings with two additional ep-oxy ring systems and a chloro-phen...
متن کاملTwo New Monoterpenes from Tithonia diversifolia and Their Anti-Hyperglycemic Activity
Two new monoterpenes: ((1S,2R,3R,5S)-2-hydroxymethyl-6,6-dimethylbicyclo[3.1.1]heptane-2,3diol (1) and (3R)-6,6-dimethyl-4-methylenebicyclo[3.1.1]heptane-1,3-diol-3-O-β-D-glucopyranoside (2), along with three known compounds, namely, sobrerol (3), (1R,2S,5S)-2,8-p-menth-diol (4) and (lR,5S)-10hydroxyverbenon (5), were isolated from aerial part of Tithonia diversifolia. Their structures were det...
متن کامل(1S,3R,8R)-2,2-Dichloro-3,7,7,10-tetramethyltricyclo[6.4.0.01,3]dodec-9-en-11-one
The title compound, C16H22Cl2O, was synthesized from β-himachalene (3,5,5,9-tetra-methyl-2,4a,5,6,7,8-hexa-hydro-1H-benzo-cyclo-heptene), which was isolated from the essential oil of the Atlas cedar (Cedrus Atlantica). The mol-ecule is built up from fused six- and seven-membered rings and an additional three-membered ring arising from the reaction of himachalene with di-chloro-carbene. The six-...
متن کاملCrystal structure of (1S,3R,8R,9R)-2,2-dichloro-3,7,7-trimethyl-10-methylenetricyclo[6.4.0.01,3]dodecan-9-ol
The title compound, C16H24Cl2O, was synthesized by treating (1S,3R,8S,9R,10S)-2,2-di-chloro-3,7,7,10-tetra-methyl-9,10-ep-oxy-tri-cyclo-[6.4.0.0(1,3)]dodecane with a concentrated solution of hydro-bromic acid. It is built up from three fused rings: a cyclo-heptane ring, a cyclo-hexyl ring bearing alkene and hy-droxy substituents, and a cyclo-propane ring bearing two chlorine atoms. The asymmetr...
متن کاملFive New Cytotoxic Metabolites from the Marine Fungus Neosartorya pseudofischeri.
The marine fungus Neosartorya pseudofischeri was isolated from Acanthaster planci from the South China Sea. In a preliminary bioactivity screening, the crude methanol extract of the fungal mycelia showed significant inhibitory activity against the Sf9 cell line from the fall armyworm Spodoptera frugiperda. Five novel compounds, including 5-olefin phenylpyropene A (1), 13-dehydroxylpyripyropene ...
متن کامل