Natural products fluorous mixture synthesis

The application of fluorous mixture synthesis (FMS) for deriving natural products and their stereoisomers was demonstrated by the total synthesis of all 16 stereoisomers of the pine sawfly sex pheromoned ... 

Fluorous Mixture Synthesis (FMS) of Drug-like Molecules and Enantiomers, Stereoisomers, and Analogues of Natural Products... 

Fluorous chemistry integrates the characteristics of solution-phase reactions and the phase tag strategy developed for solid-phase chemistry [7-15], Perfluoroalkyl chains instead of polymer beads are used as the phase tags to facilitate the separation process. In 2001 the Curran group first reported the concept of fluorous mixture synthesis (FMS) for solution-phase library synthesis [16], FMS is able to produce individual pure compounds without the effort of deconvolution. It adapts literature procedures to synthesize complex natural products, their enantiomers and diastereomers. FMS can also be used for the development of new synthetic protocols and to make novel drug-like molecules [17, 18],... 

Curran and co-workers have synthesized four closely related candidate stereoisomers for cytostatin (22) using the technique of fluorous mixture synthesis." They proved, by a combination of NMR, TLC, and optical rotation experiments and the process of elimination, that three of the isomers were not cytostatin (22b, 22c and 22d). Thus, they confirmed the structure (22a) possessing the absolute configuration of 45, 55, 65, 95,105, 115 for this important, natural product that inhibited lung metastasis of melanoma cells in mice and displaying potent cytotoxic activity toward leukemia cell lines. 

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