A Flexible Enantioselective Synthesis of the Isofurans

Recently, the isolation of a new class of human arachidonic acid tetrahydrofuran oxidation products,
the isofurans (IsoF's), was reported. These new compounds are available from natural sources only
in microgram quantities as mixtures. The enantioselective preparation of a versatile epoxide
intermediate and its conversion to the enantiomerically pure isofurans SC-Δ13-9-IsoF and 15-epi-SC-Δ13-9-IsoF are described. This synthesis will make these metabolites available for physiological
evaluation.