A stereoselective synthesis of silylated epoxycyclopentanols bearing four contiguous stereogenic centers

A palladium-catalyzed Tsuji–Trost alkylation of (E)-2-triethylsilyl-1,4-diacetoxy-but-2-ene with tert-butyl methyl malonate has been performed in excellent chemo and stereoselectivities. The allylated product has been further transformed in few steps in silylated epoxycyclopentanols bearing four controlled stereogenic carbons. The key reaction is a mild tandem oxidation–aldolization induced by DMP or IBX reagents.