Formal synthesis of (−)-anisomycin based on stereoselective nucleophilic substitution along with 1,2-aryl migration

The stereoselective conversion of (4R)-5-hydroxy-4-(4′-methoxyphenyl)-2(E)-pentenoate into the (4S)-4-hydroxy-5-(4′-methoxyphenyl)-2(E)-pentenoate using the AgNO3/MS 4 Å/MeNO2 system was accomplished along with complete inversion at the C4-position, and the synthesis of the intermediate for the chiral synthesis of (−)-anisomycin from based on osmium tetroxide-catalyzed stereoselective hydroxylation was achieved.