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J Org Chem. 2004 May 28;69(11):3950-2.

Iron-catalyzed cross-coupling reactions. A scalable synthesis of the immunosuppressive agent FTY720.

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1
Max-Planck-Institut für Kohlenforschung, D-45470 Mülheim/Ruhr, Germany fuerstner@mpi-muelheim.mpg.de

Abstract

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.

PMID:
15153030
DOI:
10.1021/jo049885d
[Indexed for MEDLINE]
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