Expeditious synthesis of enantiopure symmetrical macroheterocycles by ring-closing metathesis of ether and tether-linked 1,2-O-isopropylidenefuranosides

Bis-olefinic symmetrical carbohydrate derivatives were prepared by joining two 1,2-O-isopropylidenefuranose units either through an ether linkage or by a tether of variable size. The ring-closing metathesis (RCM) of these substrates using Grubbs' first-generation catalyst led to the synthesis of enantiopure symmetrical macroheterocycles containing nine- to twenty-five-membered rings fused to the 1,2-O-isopropylidenefuranose ring. (c) 2005 Elsevier Ltd. All rights reserved.