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The synthesis of 3‐hydroxymethyldibenzo[ b,f ]thiepin 5,5‐dioxide, a prostaglandin antagonist
Author(s) -
Hands David,
Marley Hugh,
Skittrall Stephen J.,
Wright Stanley H. B.,
Verhoeven Thomas R.
Publication year - 1986
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570230513
Subject(s) - chemistry , carboxylation , antagonist , yield (engineering) , ketone , prostaglandin , tricyclic , organic chemistry , medicinal chemistry , catalysis , biochemistry , materials science , receptor , metallurgy
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 purification, in high yield.