Chiral Synthons from the Iridoid Glucoside Antirrhinoside − Synthesis of a Carbocyclic Homonucleoside Analogue

Abstract

The synthetic modification of the natural cyclopentanoid monoterpene glucoside antirrhinoside is reported. Some stereoselective modifications have been performed on the bicyclic iridoidic ring, resulting in opening of the dihydropyran ring. A series of chiral synthons having a highly oxygenated cyclopentanoid ring has been prepared, which could be used in the synthesis of nucleoside analogues. We describe herein the synthesis of an acyclovir derivative (DA-146) as an example.