Synthetic research of hepoxilins. I. Synthesis of hepoxilins B3 via the polyacetylenic approach and the configurational assignment of the carbinolic centre

P. M. Demin, L. L. Vasil'eva, M. A. Lapitskaya, Yu. Yu. Belosludtsev, 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 hepoxilins (HX) B3, mediators of the insulin release from pancreas, has been carried out by a new route via polyacetylenic intermediates. The configurations of hydroxyl group in epimeric HXB3 were determined. (10R, 11R, 12S)-Diastereomer of HXB3 and its methyl ester are more polar on silica gel, and ButMe2Si-ether of the latter is less retentive in GLC than the corresponding (10S)-diastereomeric derivatives.

Russian Journal of Bioorganic Chemistry 1990, 16 (8):1125-1133

Full Text (PDF, in Russian)