Model multifunctional epoxides related to hepoxilin A

Vasu Nair
Tamera S. Jahnke, Missouri State University


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.