Conversion of a silylated hemiacetal into an α-bromoether using trimethylsilylbromide. Synthesis of platelet activating factor antagonist L-659,989

Article abstract of DOI:10.1016/S0040-4039(00)97214-9

An efficient synthesis of platelet activating factor antagonist L-659,989 has been achieved in ten steps from commercially available 5-iodovanillin. The key transformation converts a silylated hemi-acetal into an α-bromoether followed by a highly stereose