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Stereoselective synthesis and conformational analysis of aromatic C-thionucleosides

✍ Scribed by Ernesto Juárez; Adriana García; Herbert Hommer; Magali Salas; Barbara Gordillo

Publisher
John Wiley and Sons
Year
2006
Tongue
English
Weight
785 KB
Volume
17
Category
Article
ISSN
1042-7163

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✦ Synopsis

Abstract

Tetrahydrothiophene derivatives 2a–2d, which are useful intermediates in the synthesis of C‐thionucleosides, were obtained by a tandem strategy that involves the base‐catalyzed conjugate addition of ethyl 2‐mercaptoacetate to trans‐cinnamaldehyde followed by cyclization. The solvent and the nature of the amine used as Lewis base influence the stereo‐ selectivity of the reaction. The reduction of each isolated derivative 2a–2d was performed with LiAlH~4~ to afford C‐thionucleosides 3a–3d. The configuration and conformation of each diastereomer 2a–2d and 3a–3d was assigned by means of the analysis of vicinal proton–proton coupling constants. The X‐ray structure of 2d, 3a, and 3b confirmed the configuration assigned to each isomeric tetrahydrothiophenes. © 2006 Wiley Periodicals, Inc. Heteroatom Chem 17:289–298, 2006; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/hc.20205

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