A convenient synthesis of immunosuppressive agent FTY720 (1) using the Petasis reaction was developed. 4-Octylbenzaldehyde (9) was converted into 1-ethenyl-4-octylbenzene (11) by two-step synthesis. Hydroboration of 11 using catecholborane and hydrolysis gave (E)-2-(4-octylphenyl)vinylboronic acid (4). The Petasis reaction of 4, dihydroxyacetone (3), and benzylamine following catalytic hydrogenation afforded FTY720 (1).

A Convenient Synthesis of Immunosuppressive Agent FTY720 Using the Petasis Reaction. -As shown by the synthesis of (IV), dihydroxyacetone (I) is a good carbonyl component for the Petasis reaction. Thus, the reaction is used for a convenient synthesis of the known immunosuppressive agent FTY720 (X). -(SUGIYAMA, S.; ARAI, S.; KIRIYAMA, M.; ISHII*, K.; Chem. Pharm. Bull. 53 (2005) 1, 100-102; Meiji Pharm. Univ., Kiyose, Tokyo 204, Japan; Eng.) -M. Bohle 31-092