EPOXYOXOENE FATTY ESTERS - KEY INTERMEDIATES FOR THE SYNTHESIS OF LONG-CHAIN PYRROLE AND FURAN FATTY ESTERS

The reaction of epoxyoxoene fatty esters, methyl (Z)-9,10-epoxy-13-oxo -(E)-11 -octadecenoate (1) and methyl (Z)-12,13-epoxy-9-oxo-(E)-10-oct adecenoate (2), with glycine methyl ester in the presence of a basic r esin was studied to establish if these compounds might be useful inter mediates in the preparation of long-chain pyrrole fatty esters. Produc tion of C-18 pyrrole fatty esters and fragmentation products with the pyrrole ring were isolated and identified in the reaction. In addition , furanoid derivatives with analogous structures were also detected an d identified. Formation of these last compounds was induced by the bas ic resin and the same compounds were also produced in a reaction mixtu re incubated in the absence of the amino acid. The results found in th is study show that epoxyoxoene fatty esters 1 and 2 may be used in the preparation of both long-chain pyrrole and furan fatty acids. Althoug h their existence in nature is as yet unclear, the mass spectra result s obtained in this study provide the basis for detection and identific ation of this type of long-chain pyrrole and furan fatty acids by gas chromatography coupled with mass spectrometry.