Stereoselective synthesis of (2R,3S,4S,5R)-trans-3,4-dihydroxy-5-(4-fluorophenoxymethyl)-2-(1-N-hydroxyureidyl-3-butyn-4-yl)tetrahydrofuran and (2R,3S,4S,5R)-trans-5-ethynyl-2(4-fluorophenoxymethyl)-3,4-O-isopropylidene tetrahydrofuran from mannose d

摘要

Stereoselective synthesis of pharmaceutically interesting chiral tetrahydrofurans starting from mannose diacetonide is reported. A 1,4-diol system derived from mannose diacetonide, through a Mitsunobu reaction was stereo specifically cyclized to give chiral tetrahydrofurans. Both the C-1 and C-4 centers Of D-mannose are successfully exploited to install the requisite side chains. (C) 2005 Elsevier Ltd. All rights reserved.