Bio-inspired synthesis of rare and unnatural carbohydrates and cyclitols through strain driven epimerization??
Chemical Communications Pub Date: 2014-03-11 DOI: 10.1039/C4CC00868E
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.
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Journal Name：Chemical Communications
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CAS no.: 89640-58-4
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