Issue 44, 2015

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

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

Supplementary files

Article information

Article type
Paper
Submitted
31 Jul 2015
Accepted
04 Sep 2015
First published
04 Sep 2015

Org. Biomol. Chem., 2015,13, 10904-10916

Author version available

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

R. A. A. AL-Shuaeeb, G. Galvani, G. Bernadat, J. Brion, M. Alami and S. Messaoudi, Org. Biomol. Chem., 2015, 13, 10904 DOI: 10.1039/C5OB01603G

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