3-Hydroxy-3-methylglutaryl-coenzyme A reductase inhibitors. I. Structural modification of 5-substituted 3, 5-dihydroxypentanoic acids and their lactone derivatives

…, WF Hoffman, AW Alberts, EJ Cragoe Jr…

Index: Stokker; Hoffman; Alberts; Cragoe Jr.; Deana; Gilfillan; Huff; Novello; Prugh; Smith Journal of Medicinal Chemistry, 1985 , vol. 28, # 3 p. 347 - 358

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Citation Number: 108

Abstract

Chemistry. The compounds prepared for this study are listed in Tables 1-111. Their syntheses from the corresponding aldehydes, exemplified by 2, are shown in Schemes 1- 111. Condensation of aldehyde 2 with the dianion of ethyl acetoacetate16 followed by borohydride reduction, basic hydrolysis, acidification, and azeotropic removal of water provided a mixture of the trans (sa (*)) and cis (6b (*)) lactones which subsequently was ...