Nomenclature
CAS number: 509-93-3
3,3a,4,5,6,6a,9a,9b-Octahydro-6,9a-dimethyl-3-methyleneazuleno[4,5-
b]furan-2,9-dione; 6β-hydroxy-4-oxo-10α
H-ambrosa-2,11(13)-dien-12-oic
acid γ-lactone.
C
15H
18O
3; mol wt 246.30.
C 73.15%, H 7.37%, O 19.49%.
Description and references
From herb of Ambrosia maritima L., Compositae: Abu-Shady, Soine, J. Am.
Pharm. Assoc. 42, 387 (1953); 43, 365 (1954). Structure: Bernardi, Büchi, Experientia 13, 466 (1957); Sorm et al., Collect. Czech. Chem. Commun. 24, 1548 (1959); Nerz et al., J. Am. Chem. Soc. 84, 2601 (1962).
Absolute configuration: Emerson et al., Tetrahedron Lett. 1966, 6151.
Stereospecific total synthesis of (±)-form: P. A. Grieco et
al., J. Am. Chem. Soc. 99, 7393 (1977).
Properties
Crystals from alc, mp 146°. [α]D22 154.50° (c = 2 in alcohol). uv max (95% ethanol): 217, 324 nm (ε 13465; 36). Very sol in chloroform; sol in alc,
benzene, sparingly sol in ether, petr ether. Practically insol in
water, cold dil NaOH, dil acids.Derivative
(±)-Form.
Properties
mp 188-190°.