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 in individual pure form offers efficiency advantages that are negated by the difficulty in separating and identifying the components of the final mixture. Here, a strategy for mixture synthesis that addresses these separation and identification problems is presented. A series of organic substrates was 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 tagged products were then demixed by fluorous chromatography (eluting in order of increasing fluorine content) to provide the individual pure components of the mixture, which were detagged to release the final products.
Luo
Z
Z
Department of Chemistry and Center for Combinatorial Chemistry, University of Pittsburgh, Pittsburgh, PA 15260, USA.
Zhang
Q
Q
Oderaotoshi
Y
Y
Curran
D P
DP
D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D002845:Chromatography; D002850:Chromatography, Gel / Q000379:methods*; D020650:Combinatorial Chemistry Techniques; D005461:Fluorine / Q000032:analysis; D009930:Organic Chemicals / Q000138:chemical synthesis* / Q000302:isolation & purification; D013057:Spectrum Analysis; D013237:Stereoisomerism
D000470:Alkaloids; D009930:Organic Chemicals; D005461:Fluorine; C008325:mappicine