Linearization of carbohydrate derived polycyclic frameworks?

RSC Advances Pub Date: 2014-07-23 DOI: 10.1039/C4RA04845H

Abstract

We report easy access to carbohydrate derived diverse tricyclic skeletons which could be beneficial for exploring polyfunctionalized chiral alicycles. The key reaction to assemble a sugar fused tricyclic core is intermolecular tandem esterification and 1,3-dipolar cycloaddition. The framework was elaborated using amide forming reactions, opening of isoxazolidine rings followed by N and O-acylations. The sequences provide distinct, spatially separated and encoded chemical entities that may pave the way to investigate cell functions.

Graphical abstract: Linearization of carbohydrate derived polycyclic frameworks
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