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Carbon‐14 methylation of the 2‐methylbutyryl side chain of mevinolin and its analogs
Author(s) -
Prakash S. R.,
Ellsworth R. L.
Publication year - 1988
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/jlcr.2580250803
Subject(s) - chemistry , side chain , ammonium , alkylation , methylation , methyl iodide , potassium , carbon chain , organic chemistry , high performance liquid chromatography , stereochemistry , biochemistry , catalysis , polymer , gene
Abstract A one step procedure for the preparation of labeled mevinolin analogs 4 , 10 and 15 possessing the 2,2‐dimethylbutyryloxy side chain is described. The lactones 1 , 7 and 13 were converted into potassium salts of their corresponding di or trihydroxy carboxylic acids from which anionic ester enolates were generated and alkylated with [ 14 C]methyl iodide. Workup and purification by reverse phase HPLC provided radiochemically pure 4 , 10 and 15 . The labeled lactones were converted into ammonium salts of their corresponding di or trihydroxy acids.