Abstract
A efficient process for the commercial preparation of the therapeutically important cholesterol lowering drug synvinolin (2: simvastatin, ZOCOR) from mevinolin(1: lovastatin, MEVACOR) is reported. The synthesis relies upon deactivation of the δ-lactone carbonyl toward enolization via conversion to the bis [(tert-butyldimethylsilyl) oxyl] butylamide 7. An extremely high conversion (99.7%) ester enolate alkylation of 7 affords 8 and 9. Subsequent desilylation and intramolecularly assisted basic amide hydrolysis in the presence of the dimethylbutyrate ester moiety yields 12, which is lactonized to 2
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