Opening of the lactone ring of silylated mevinolin (I) with the naphthalenylmethylamine (II) produced the hydroxy amide (III). After conversion of the hydroxyl group of (III) to the corresponding mesylate (IV), intramolecular cyclization in the presence of sodium bis(trimethylsilyl)amide furnished lactam (V). Finally, desilylation of (V) under acidic conditions gave rise to the title compound.
Dehydration of mevinolin (I) by means of acetic anhydride in the presence of DMAP gives rise to the conjugated lactone (II). Subsequent reaction of (II) with 4-(tert-butyldimethylsilyloxy)-3-methoxybenzylamine (III) in MeOH leads to the amino hydroxy ester (IV). This is then treated with carbonyldiimidazole in DMF to produce the cyclic carbamate (V). Finally, ester group aminolysis with simultaneous desilylation with ethanolamine in boiling MeOH furnishes the title compound.