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A short synthesis of substituted β-hydroxy γ-butyrolactones and 2-deoxyhexofuranosides

✍ Scribed by Jean-Marc Escudier; Michel Baltas; Gorrichon Liliane

Publisher
Elsevier Science
Year
1992
Tongue
French
Weight
239 KB
Volume
33
Category
Article
ISSN
0040-4039

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✦ Synopsis

l'he development of new synthetic routes to deoxysugars and C-nucleosides is the subject of intensive ress~ch since significant antiviral and antitumor activities have been observed with these cornpounds.l-6 Lkoxysugars are also useful intcnnediates in the synthesis of optically active cornpounds even if rheir availability is rathc.r limited compared to some other carbohydrate precursors. 8 We now present a flexible syrlthebis of substituted P=hydroxy y-butymlactones 3 and 2-deoxyhexoses 4 by intranlolccular cyrlisation of uornpo14r1ds 2, which were readily synthetized by addition of t-bury1 lithioacetates to optically active a,13epoxyaldehydes 1.9 R'

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