Title: Vernolepin
CAS Registry Number: 18542-37-5
CAS Name: [3aR-(3aa,4a,5aa,9aa,9bb)]-5a-Ethenyloctahydro-4-hydroxy-3,9-bis(methylene)-2H-furo[2,3-f][2]benzopyran-2,8(3H)-dione
Molecular Formula: C15H16O5
Molecular Weight: 276.28
Percent Composition: C 65.21%, H 5.84%, O 28.96%
Literature References: The first recognized naturally occurring elemanolide dilactone; a sesquiterpene lactone with tumor inhibiting properties. Isoln from Vernonia hymenolepsis A. Rich, Compositae and structure: S. M. Kupchan et al., J. Am. Chem. Soc. 90, 3596 (1968); structural elucidation: eidem, J. Org. Chem. 34, 3903 (1969). Biological properties: S. M. Kupchan et al., J. Med. Chem. 14, 1147 (1971). Approach to stereosynthesis of (+)-form: H. Iio et al., Tetrahedron 35, 941 (1979); K. Kondo et al. Tetrahedron Lett. 34, 4219 (1993). Total synthesis of (±)-form: P. A. Grieco et al., J. Am. Chem. Soc. 98, 1612 (1976); F. Zutterman et al., Tetrahedron 35, 2389 (1979).
Properties: Crystals from chloroform-petr ether, mp 181-182°. [a]D28 +72° (c = 1.04 in acetone). uv max (methanol): 208 nm (e 20300).
Melting point: mp 181-182°
Optical Rotation: [a]D28 +72° (c = 1.04 in acetone)
Absorption maximum: uv max (methanol): 208 nm (e 20300)
Derivative Type: (±)-Form
CAS Registry Number: 59598-29-7
Properties: Crystals from chloroform, mp 210-211°.
Melting point: mp 210-211°
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