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Synthesis 2006(24): 4163-4166  
DOI: 10.1055/s-2006-950351
PAPER
© Georg Thieme Verlag Stuttgart · New York

Efficient Syntheses of Thiono and Dithio Analogues of Tetronic Acid

Raphaël Labruère, Stéphanie Desbène-Finck, Philippe Helissey, Sylviane Giorgi-Renault*
Laboratoire de Chimie Thérapeutique, UMR CNRS-Université René Descartes (Paris 5), Faculté des Sciences Pharmaceutiques et Biologiques, 4 avenue de l’Observatoire, 75270 Paris Cedex 06, France
Fax: + 33(1)43291403; e-Mail: Sylviane.Giorgi-Renault@univ-paris5.fr;
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Publication History

Received 20 July 2006
Publication Date:
02 November 2006 (online)

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Abstract

Thiono and dithio lactone analogues of 4-hydroxyfuran-2(5H)-one (tetronic acid) were synthesized in three steps from tetronic acid and thiolotetronic acid. Their usefulness in pharmacomodulation were exemplified by the synthesis of thio analogues of 4-aza-2,3-didehydropodophyllotoxins.

Key words

tetronic acid - thionolactones - dithiolactones - azapodophyllotoxins - Lawesson’s reagent