1977. Cephalonic Acid

Nomenclature

CAS number: 18456-04-7
8-Hydroxy-5-oxoophiobola-3,6,19-trien-25-oic acid; ophiobolin D.
C25H36O4; mol wt 400.55.
C 74.96%, H 9.06%, O 15.98%.

Description and references

Minor antibiotic metabolite produced by Cephalosporium caerulens. Exhibits weak activity against Staphylococcus aureus. Isolation, structure elucidation and physical data: Itai et al., Tetrahedron Lett. 1967, 4111; Nozoe et al., ibid. 4113. Crystal structure: Itai et al., Acta Crystallogr. 25B, 872 (1969). Synthetic studies on related compounds: P. C. Dutta, T. K. Das, Synth. Commun. 6, 253 (1976); W. G. Dauben, D. S. Hart, J. Org. Chem. 42, 922 (1977); R. K. Boeckman et al., ibid. 3630.

Chemical structure

Properties

Solid, mp 139°. [α]D +76.2° (c = 0.54 in chloroform). uv max: 259 nm (ε 11700).