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

G Seidel, D Laurich, A Fürstner - The Journal of organic chemistry, 2004 - ACS Publications
G Seidel, D Laurich, A Fürstner
The Journal of organic chemistry, 2004ACS Publications
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.
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.
ACS Publications