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A New Method for the Synthesis of Antihypercholesterolemic Agent Simvastatin
Author(s) -
Dabak Kadir,
Adiyaman Mustafa
Publication year - 2003
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.200390066
Subject(s) - chemistry , simvastatin , lovastatin , alkylation , chromatography , organic chemistry , cholesterol , pharmacology , biochemistry , catalysis , medicine
Abstract A new synthetic method for the preparation of the cholesterol‐lowering drug simvastatin from the naturally occurring lovastatin is reported. The synthesis employs first the protection of the OH group of lovastatin ( 1 ) and then the protection of the lactone CO group to prevent enolization via conversion to the orthoesters 4a and 4b . Alkylation of the 2‐methylbutyrate side chain is then successfully achieved. Removal of the protecting groups affords antihypercholesterolemic agent simvastatin ( 2 ).