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The synthesis of carbon-14 labeled pravastatin

✍ Scribed by M. A. Wallace; D. C. Dean; R. L. Ellsworth; D. G. Melillo; T. Marks; R. F. White

Publisher
John Wiley and Sons
Year
1993
Tongue
French
Weight
329 KB
Volume
33
Category
Article
ISSN
0022-2135

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✦ Synopsis

Abstract

As asymmetric route to [^14^C]β‐hydroxycompactin 1 bearing the (S)‐2‐methyl‐[1‐^14^C]butanoate side chain has been developed. Methylation of [N‐[1‐^14^C]butyryl‐4‐(S)‐phenylmethyl‐2‐oxazolidinone 4 afforded a 95:5 mixture of diastereomeric [N‐(S,R)‐2‐methyl‐[1‐^14^C]butyryl]‐4‐(S)‐phenylmethyl‐2‐oxazolidinones 5,6 which were separated by preparative HPLC. Oxidative cleavage of 5 afforded optically pure (S)‐2‐methyl‐[1‐^14^C]butanoic acid. Acylation of alcohol 9 with optically pure (S)‐2‐methyl‐[1]^14^C]butyryl chloride afforded ester 10. Removal of the silyl either produced diastereomerically pure compactin 11. Hydroxylation was carried out by biotransformation with Mucor hiemelus to afford diastereomerically pure [[1‐^14^C]butanoate]β‐hydroxycompactin, [^14^C]Pravastatin 1.

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