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HEPOXILINS A 3 CONFIGURATION AND THEIR SYNTHESIS BY MEANS OF HEPOXILINS B 3 ISOMERIZATION
P. M. DEMIN, L. L. VASIL'EVA*, Yu. Yu. BELOSLUDTSEV, G. I. MYAGKOVA, K. K. PIVNITSKY *
M. V. Lomonosov Institute of Fine Chemical Technology, Moscow; * Institute of Experimental Endocrinology and Hormone Chemistry, Academy of Sciences of the USSR, Moscow
Abstract: Hepoxilins (HX) A3 methyl esters epimeric at C8 are synthesized by the solvolysis of epimeric HXB3 methyl ester mesylates. Each of individual HXB3 epimers produces a mixture of HXA3 epimers, their ratio being exactly opposite in two case (S N 2' mechanism). The known preference of syn-substitution in this mechanism allows one to deduce, 8R-configuration for the more polar epimer of HXA3 ester.
Russian Journal of Bioorganic Chemistry 1990, 16 (4):571-572