Premium
Chiral Synthons from the Iridoid Glucoside Antirrhinoside − Synthesis of a Carbocyclic Homonucleoside Analogue
Author(s) -
Bianco Armandodoriano,
Celona Diana,
Di Rita Sara,
Guiso Marcella,
Melchioni Cristiana,
Umani Floriana
Publication year - 2001
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/1099-0690(200111)2001:21<4061::aid-ejoc4061>3.0.co;2-3
Subject(s) - synthon , chemistry , bicyclic molecule , stereochemistry , monoterpene , dihydropyran , stereoselectivity , ring (chemistry) , glucoside , derivative (finance) , iridoid , organic chemistry , glycoside , catalysis , medicine , alternative medicine , pathology , financial economics , economics
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.