Synthesis of the Enediol Isofurans,Endogenous Oxidation Products of Arachidonic Acid

摘要

Isofurans(IsoF's)are a new class of human arachidonic acid oxidation products.They are produced in vivo by a free radical mechanism,independent of the cyclooxygenase enzymes.These new compounds are available from natural sources only in microgram quantities as mixtures.The enantioselective preparation of two enediol isofurans,15-epi-ent-SC-DELTA~(13)-8-IsoF and ent-SC-DELTA~(13)-8-IsoF,is described.A key transformation in the synthesis is the selective cascade cyclization of a diol epoxide benzenesulfonate to give the substituted tetrahydrofuran skeleton of the isofurans.This synthesis will make these metabolites available for physiological evaluation.