Synthetic research of hepoxilins. 2. Hepoxilins A3: synthesis, configuration and composition of the hydrolysis products trioxilins A3

P. M. Demin, L.L. Vasil'eva, G. I. Myagkova, K. K. Pivnitsky

M. V. Lomonosov Institute of Fine Chemical Technology, Moscow, Institute of Experimental Endocrinology, All-Union Endocrinology Research Centre, Academy of Medical Sciences of the USSR, Moscow

Abstract: A synthesis of C8-epimeric hepoxilins (HX) A3 esters was carried out by the allylic rearrangement of C10-epimeric HXB3 esters in the course of their mesylates hydrolysis. (8R)- and (8S)-configuration are assigned to the more and less polar epimers of HXA3 methyl esters, respectively, on the basis of the independently confirmed syn-stereoselecti-vity of the allylic mesylatesolvolysis. The composition of the HXA3 oxirane cycle hydrolysis products, trioxilins (TrX) A3, was investigated. The formation of two sets of regio-isomers, viz., (8,9,12)- and (8,11l,12)-TrXA3, was demonstrated, each one being a mixture of four compounds stereoisomeric at C8 and C9/C11. Structures and configurations at C8 of the individual TrXA3 are identified.

Russian Journal of Bioorganic Chemistry 1991, 17 (8):1133-1140

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