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Iron-Catalyzed Cross-Coupling Reactions. A Scalable Synthesis of the Immunosuppressive Agent FTY720

2004; American Chemical Society; Volume: 69; Issue: 11 Linguagem: Inglês

10.1021/jo049885d

1520-6904

Günter Seidel, Daniel Laurich, Alois Fürstner,

Synthesis and Catalytic Reactions

A chemo- and regioselective cross-coupling reaction of the functionalized aryl triflate 5 with octylmagnesium bromide catalyzed by cheap, nontoxic, and environmentally benign Fe(acac)3 sets the basis for a practical and scaleable synthesis of the octylbenzene derivative 6, which serves as a key building block for the preparation of FTY720 (1). This 2-amino-1,3-propanediol derivative shows highly promising immunosuppressive properties and is currently in human clinical phase III trials.