Title: Plumericin
CAS Registry Number: 77-16-7
CAS Name: (3E,3aS,4aR,7aS,9aS,9bS)-3-Ethylidene-3,3a,7a,9b-tetrahydro-2-oxo-2H,4aH-1,4,5-trioxadicyclopent[a,hi]indene-7-carboxylic acid methyl ester
Molecular Formula: C15H14O6
Molecular Weight: 290.27
Percent Composition: C 62.07%, H 4.86%, O 33.07%
Literature References: A sesquiterpenoid, exhibiting in vitro activity against fungi, some bacteria including Mycobacterium tuberculosis 607. Isoln from roots of Plumeria multiflora Muell.-Arg., Apocynaceae, also from roots of P. rubra var. alba: J. E. Little, D. B. Johnstone, Arch. Biochem. 30, 445 (1951); from Allamanda cathartica Linn., Apocynaceae: B. R. Pai et al., Indian J. Chem. 8, 851 (1970). Structure, physical properties and IR, 1HNMR spectra: G. Albers-Schönberg, H. Schmid, Helv. Chim. Acta 44, 1447 (1961). Synthetic approach: J. K. Whitesell et al., Synth. Commun. 7, 355 (1977). Biomimetic total synthesis of (±)-form: B. M. Trost et al., J. Am. Chem. Soc. 105, 6755 (1983); eidem, ibid. 108, 4974 (1986). Alternate synthesis of (±)-form: eidem, ibid. 4965; K. E. B. Parkes, G. Pattenden, J. Chem. Soc. Perkin Trans. 1 1988, 1119.
Properties: Narrow, rectangular plates from alc, toluene or methylene chloride + ether, dec 211.5-212.5°. Sublimes in high vacuum at 160-180°. [a]D25 +197.5 ±2° (c = 0.982 in chloroform). uv max (ethanol): 214-215 nm (log e 4.24). Sol in chloroform; slightly sol in methanol, alc, ether, acetone, benzene. Practically insol in petr ether, water.
Optical Rotation: [a]D25 +197.5 ±2° (c = 0.982 in chloroform)
Absorption maximum: uv max (ethanol): 214-215 nm (log e 4.24) |