Issue 51, 2014

Bio-inspired synthesis of rare and unnatural carbohydrates and cyclitols through strain driven epimerization

Abstract

We report a bio-inspired, strain driven epimerization of trans-ketals to cis-ketals through an enolate intermediate. Swern oxidation of a hydroxyl group adjacent to a trans-ketal effects both oxidation and its epimerization to cis-ketal. This novel and general strategy allows inversion of up to three contiguous stereocenters and has been illustrated by the synthesis of several unnatural/rare isomers of carbohydrates/cyclitols from their naturally abundant isomers.

Graphical abstract: Bio-inspired synthesis of rare and unnatural carbohydrates and cyclitols through strain driven epimerization

Supplementary files

Article information

Article type
Communication
Submitted
02 Feb 2014
Accepted
11 Mar 2014
First published
11 Mar 2014

Chem. Commun., 2014,50, 6707-6710

Author version available

Bio-inspired synthesis of rare and unnatural carbohydrates and cyclitols through strain driven epimerization

R. Mohanrao, A. Asokan and K. M. Sureshan, Chem. Commun., 2014, 50, 6707 DOI: 10.1039/C4CC00868E

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