The Journal of Organic Chemistry

Synthesis of. alpha.-pyrones from vinylogous thiol esters and. alpha.-oxo ketene dithioacetals

RK Dieter, JR Fishpaugh

Index: Dieter, R. Karl; Fishpaugh, Jeffrey R. Journal of Organic Chemistry, 1988 , vol. 53, # 9 p. 2031 - 2046

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Citation Number: 52

Abstract

Vinylogous thiol esters and a-oxo ketene dithioacetals can be converted into a-pyrones by a strategy involving 1, 2-nucleophilic addition of ester, ketone, or hydrazone enolate anions, followed by acid-promoted rearrangement to a &keto ester, thiol ester, or acid and subsequent enol lactonization. These multistep procedures can be carried out without isolation and purification of intermediates and afford a-pyrones in good overall yields. The ...