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Diversity-oriented synthesis of fused thioglycosyl benzo[e][1,4]oxathiepin-5-ones and benzo[f][1,4]thiazepin-5(2H)-ones by a sequence of palladium-catalyzed glycosyl thiol arylation and deprotection–lactonization reactions†
Riyadh Ahmed Atto AL-Shuaeeb,Gilles Galvani,Guillaume Bernadat,Jean-Daniel Brion,Mouad Alami,Samir Messaoudi
Organic & Biomolecular Chemistry Pub Date : 09/04/2015 00:00:00 , DOI:10.1039/C5OB01603G
Abstract

An efficient synthesis of thioglycosylated benzo[e][1,4]oxathiepin-5-one and benzothiazepinone derivatives by a sequence of palladium-catalyzed glycosyl thiol arylation followed by deprotection–lactonization reactions has been reported. This diversity-oriented strategy enabled access to unknown complex cyclic scaffolds with polyhydroxylated appendages of biological interest.

Graphical abstract: Diversity-oriented synthesis of fused thioglycosyl benzo[e][1,4]oxathiepin-5-ones and benzo[f][1,4]thiazepin-5(2H)-ones by a sequence of palladium-catalyzed glycosyl thiol arylation and deprotection–lactonization reactions
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