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-Delta(13)-9-IsoF and 15-epi-SC-Delta(13)-9-IsoF are described. This synthesis will make these metabolites available for physiological evaluation.
Taber
Douglass F
DF
Department of Chemistry and Biochemistry, University of Delaware, Newark, Delaware 19716, USA. taberdf@udel.edu
Pan
Yongchun
Y
Zhao
Xia
X
D005663:Furans / Q000138:chemical synthesis*; D006801:Humans; D007536:Isomerism; D015394:Molecular Structure; D013237:Stereoisomerism
D005663:Furans