Journal of Organic Chemistry p. 4929 - 4932 (1991)
Update date:2022-08-04
Topics:
Askin, D.
Verhoeven, T. R.
Liu, T. M.-H.
Shinkai, I.
An 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)oxy>butylamide 7.An extremely high conversion (99.7percent) 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.The overall yield from 1 to 2 is 86percent.
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