Synthesis of 1,2-dioleoyl-3-(alpha-14C-1-adamantoyl)-sn-glycerol and 1-14C-adamantanecarboxylic acid

The pancreatic lipase inhibitor 1,2-dioleoyl-3-(alpha-14C-1-adamantoyl)-sn-glycerol, with a specific activity of 8 mCi/mmole, was prepared by consecutive acylation of 1,2-isopropylidene-sn-glycerol with 1-14C-adamantanecarboxylic acid chloride and oleoyl chloride. The 14C-labeled acid was conveniently prepared by carboxylation of 1-adamantanol using 14C-sodium formate in concentrated sulfuric acid.