Efficient synthesis of the immunosuppressive agent FTY720

The concise and practical synthesis of the biologically important FTY720 was achieved employing the palladium-catalyzed Sonogashira coupling reaction as a key step. The commercial tris(hydroxymethyl)aminomethane was converted to alkyne 2 via a three-step synthesis. The coupling reactions of alkyne 2 with aryl iodide 3, followed by subsequent hydrogenation of the internal alkyne and removal of the protecting groups provided FTY720 in high overall yield.