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Incorporation of 2(S)-methylbutanoic acid-1-14C into the structure of mevinolin

✍ Scribed by Alvin K. Willard; Robert L. Smith

Publisher
John Wiley and Sons
Year
1982
Tongue
French
Weight
334 KB
Volume
19
Category
Article
ISSN
0022-2135

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✦ Synopsis

Abstract

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.

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