Synthesis of perfluoroalkyl steroids as CO-emulsifying agents for 1-bromoperfluorooctane and other perfluorocompounds

Abstract

Abstract Syntheses of steroids substituted with perfluoroalkyl groups at C-3, C-7, and C-20 positions on the steroid nucleus are described. Synthetic methods employed included coupling of perfluoroalkylcopper with allylic bromides and Grignard reactions. Free radical additions of perfluoroalkyl iodide to unsaturated steroids and reaction of perfluoroalkyl Grignard reagents with 6-ketosteroid were unsuccessful. Perfluoroalkyl -substituted steroids are desired for testing as co-emulsifying agents in perfluorooctyl bromide/water emulsions which are used as blood substitutes ( synthetic blood ). A rationale for the choice of perfluorooctyl bromide as the oxygen-carrying agent in the fluorocarbon-based blood substitute and on the use of perfluoroalkyl-substituted steroids as co-emulsifying agents is also reported.