An efficient synthetic route to 2-(1,2-dithiolan-3-yl)acetic acid. Trisnorlipoic acid and amide derivatives

A simple, efficient synthesis of 2-(1,2-dithiolan-3-yl)acetic acid from Meldrum's acid, acrolein and thioacetic acid is described. The isopropyldene 2,4- bis(acetylthio)butane-1,1-dicarboxylate formed in the three-component, single container process, can be methanolized to the corresponding dim...

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Bibliographic Details
Published inTetrahedron letters Vol. 38; no. 33; pp. 5785 - 5788
Main Authors Chen, Yaun-Shek, Lawton, Richard G
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 18.08.1997
Elsevier
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
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Summary:A simple, efficient synthesis of 2-(1,2-dithiolan-3-yl)acetic acid from Meldrum's acid, acrolein and thioacetic acid is described. The isopropyldene 2,4- bis(acetylthio)butane-1,1-dicarboxylate formed in the three-component, single container process, can be methanolized to the corresponding dimethyl ester and then hydrolyzed, oxidized to the disulfide and decarboxylated to 2-(1,2-dithiolan-3-yl)acetic acid. The acid can be converted by conventional reagents into a variety of amide derivatives. A simple, efficient synthesis of 2-(1,2-dithiolan-3-yl)acetic acid from Meldrum's acid, acrolein and thioacetic acid is described.
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(97)01319-1