Facile separation of chiral 1,3-dihydrobenzo[c]furan derivatives using a D-xylose moiety as a protecting group

Abstract

1,2-O-Isopropylidene-α-D-xylofuranose has been used to protect one aldehyde group of o-phthalaldehyde. This chiral protecting group acts as a resolving agent and this leads to separable diastereoisomers when a new stereogenic centre is created by the conversion of the second aldehyde group to a benzyloxyhydroxyethyl chain. These separated diastereoisomers were cyclised to 1,3-dihydrobenzo[c]furans with retention of chiral integrity at the C3 site thus allowing further elaboration to enantiomerically pure nucleoside analogues. © 2001 Published by Elsevier Science Ltd.