Model multifunctional epoxides related to hepoxilin A

Abstract

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.

Department(s)

Chemistry and Biochemistry

Document Type

Article

DOI

https://doi.org/10.1016/S0040-4020(01)90300-X

Publication Date

1-1-1987

Journal Title

Tetrahedron

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