1613320-24-3Relevant articles and documents
Bio-inspired synthesis of rare and unnatural carbohydrates and cyclitols through strain driven epimerization
Mohanrao, Raja,Asokan, Aromal,Sureshan, Kana M.
, p. 6707 - 6710 (2014)
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. This journal is the Partner Organisations 2014.