Fluorous mixture synthesis: A fluorous-tagging strategy for the synthesis and separation of mixtures of organic compounds

The solution-phase synthesis of organic compounds as mixtures rather than i n individual pure form offers efficiency advantages that are negated by the difficulty in separating and identifying the components of the final mixtu re. Here, a Strategy for mixture synthesis that addresses these separation and identification problems is presented. A series of organic substrates wa s tagged with a series of fluorous tags of increasing fluorine content. The compounds were then mixed, and multistep reactions were conducted to make enantiomers or analogs of the natural product mappicine. The resulting tagg ed products were then demixed by fluorous chromatography (eluting in order of increasing fluorine content) to provide the individual pure components o f the mixture, which were detagged to release the final products.