Synthesis of the enediol isofurans, endogenous oxidation products of arachidonic acid.
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-Delta13-8-IsoF and ent-SC-Delta13-8-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.
Taber
Douglass F
DF
Department of Chemistry and Biochemistry, University of Delaware, Newark, DE 19716, USA. taberdf@udel.edu
Zhang
Zhe
Z
D000438:Alcohols / Q000737:chemistry; D016718:Arachidonic Acid / Q000737:chemistry*; D003500:Cyclization; D004852:Epoxy Compounds / Q000737:chemistry; D005663:Furans / Q000138:chemical synthesis / Q000737:chemistry*; D007536:Isomerism; D015394:Molecular Structure; D010084:Oxidation-Reduction
D000438:Alcohols; D004852:Epoxy Compounds; D005663:Furans; D016718:Arachidonic Acid