Title: Arborescin
CAS Registry Number: 6831-14-7
CAS Name: (3aR,4aS,6aS,7S,9aS,9bR)-5,6,6a,7,9a,9b-Hexahydro-1,4a,7-trimethyl-3H-oxireno[8,8a]azuleno[4,5-b]furan-8(4aH)-one
Additional Names: 1,10-epoxy-6b-hydroxy-1b,5b,7a-guiai-3-en-12-oic acid g-lactone
Molecular Formula: C15H20O3
Molecular Weight: 248.32
Percent Composition: C 72.55%, H 8.12%, O 19.33%
Literature References: Ancient Greek contraceptive. Isoln from Artemisia arborescens L. and Matricaria globifera (Thunb.) Druce, Compositae: Meisels, Weizmann, J. Am. Chem. Soc. 75, 3865 (1953); Cekan et al., Collect. Czech. Chem. Commun. 25, 2553 (1960). Structure: Bates et al., Tetrahedron Lett. 1963, 1127; M. Suchy et al., Collect. Czech. Chem. Commun. 29, 1829 (1964). Synthesis and revised structure: M. Ando et al., Chem. Lett. 1978, 727. Stereochemistry: M. Ando et al., J. Org. Chem. 47, 3909 (1982).
Properties: Crystals from ethanol, mp 140-142°. [a]D20 +64° (c = 0.72 in chloroform).
Melting point: mp 140-142°
Optical Rotation: [a]D20 +64° (c = 0.72 in chloroform) |