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Incorporation of 2( S )‐methylbutanoic acid‐1‐ 14 C into the structure of mevinolin
Author(s) -
Willard Alvin K.,
Smith Robert L.
Publication year - 1982
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.2580190305
Subject(s) - chemistry , acylation , diastereomer , alcohol , cleavage (geology) , ammonium , ether , ammonium chloride , salt (chemistry) , medicinal chemistry , stereochemistry , carboxylic acid , organic chemistry , catalysis , geotechnical engineering , fracture (geology) , engineering
A route to mevinolin () bearing (S)‐2‐methylbutanoic acid ‐1‐ 14 C as the ester side chain has been developed. The structure of mevinolin () was degraded and selectively protected to provide the alcohol in three steps. Incorporation of 14 C was accomplished by acylation of alcohol with (R,S)‐2‐methylbutyryl chloride‐1‐ 14 C. Cleavage of the silyl ether protecting group in the resulting mixture of esters provided the two diastereoisomers and which were separated by reverse‐phase liquid chromatography. Mevinolin ‐ 14 C () was also converted to the ammonium salt of the corresponding dihydroxy acid.