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Practical synthesis of an enantiomerically pure synthon for the preparation of mevinic acid analogs

Authors :
Mary F. Malley
Jack Z. Gougoutas
Donald S. Karanewsky
Source :
The Journal of Organic Chemistry. 56:3744-3747
Publication Year :
1991
Publisher :
American Chemical Society (ACS), 1991.

Abstract

We report an alternative synthesis of 1 that utilizes commercially available (S)-1-phenethylamine as the source of chirality and can be used for the large-scale preparation of 1. Reaction of anhydride 4 with (S)-1-phenethylamine in the preence of triethylamine with toluene as solvent (−78°C, 4.5 h) gave a 79:21 mixture of diastereomeric acids 8a (1: title compounds)

Details

ISSN :
15206904 and 00223263
Volume :
56
Database :
OpenAIRE
Journal :
The Journal of Organic Chemistry
Accession number :
edsair.doi...........be91fd4378dd4ee80b2fb97fe42c6cbc