Iron-catalyzed cross-coupling reactions. A scalable synthesis of the immunosuppressive agent FTY720.
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.
Seidel
Günter
G
Max-Planck-Institut für Kohlenforschung, D-45470 Mülheim/Ruhr, Germany fuerstner@mpi-muelheim.mpg.de
Laurich
Daniel
D
Fürstner
Alois
A
D002384:Catalysis; D000068876:Fingolimod Hydrochloride; D006801:Humans; D007166:Immunosuppressive Agents / Q000138:chemical synthesis*; D007501:Iron / Q000737:chemistry*; D015394:Molecular Structure; D011409:Propylene Glycols / Q000138:chemical synthesis*; D013110:Sphingosine / Q000031:analogs & derivatives
D007166:Immunosuppressive Agents; D011409:Propylene Glycols; D007501:Iron; D000068876:Fingolimod Hydrochloride; D013110:Sphingosine