Model multifunctional epoxides related to hepoxilin A
An enolic epoxy fatty acid, 8,9-(S,S)-epoxy-5-hydroxy-6-dodecenoic acid, has been synthesized. This compound is a model system for the biologically important compound, hepoxilin A. The model epoxy fatty acid cyclized readily to form an epoxy lactone. Acid-catalyzed ring opening resulted in the formation of isomeric oxadienes which were structurally differentiated by comparison of their 2-D COSY NMR spectra. Thiols cleaved the epoxide ring rapidly and quantitatively. © 1987.
Chemistry and Biochemistry
Nair, Vasu, and Tamera S. Jahnke. "Model multifunctional epoxides related to hepoxilin A." Tetrahedron 43, no. 19 (1987): 4257-4264.