The synthesis of 3??hydroxymethyldibenzo [b, f] thiepin 5, 5??dioxide, a prostaglandin antagonist

D Hands, H Marley, SJ Skittrall…

Index: Hands; Marley; Skittrall; Wright Journal of Heterocyclic Chemistry, 1986 ,  vol. 23,  # 5  p. 1333 - 1337

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Citation Number: 2

Abstract

Abstract An economic synthesis of 3-hydroxymethyldibenzo [b, f] thiepin 5, 5-dioxide, a novel prostaglandin antagonist, is described. The key step in the synthesis is the formation of a carboxyphenylacetic acid by carboxylation of a toluic acid dianion, followed by cyclisation to the tricyclic ketone. Readily available starting materials are used in the synthesis and conditions have been found at each stage to give pure intermediates, requiring little ...