Abstract
Synthetic methods have been investigated to determine the best way to introduce two or more perfluoroalkyl groups (R f = C 6F 13-, C 8F 17-, or C 10F 21-) on the alpha-side of a steroid molecule. Perfluoroalkyl- alpha-substituted steroids are desired for testing as coemulsifying agents in fluorocarbon- based blood substitutes ( synthetic blood). We postulate that a monolayer of perfluoroalkyl- alpha-substituted steroid will form around a perfluorocarbon micelle and reduce the interfacial tension between the fluorocarbon and the conventionally-used emulsifying agents ( Pluronic F68 or egg-yolk phospholipid), drawn below for Pluronic F68, a block polymer of polyethylene oxide- polypropylene oxide-polyethylene oxide. Perfluoroalkyl steroids were prepared from potassium salts of steroidal alcohols and perfluoroalk-l-enes. A new esterification procedure for perfluoroalkanoic acids was developed to give tri-perfluoroalkanoic acid esters of methyl cholate (I). Combinations of synthetic methods were used to obtain desired compounds. Free-radical addition of 1-iodoperfluoroalkanes to unsaturated steroids was not useful. ▪
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