Premium
Synthesis of Aucubovir II, a New Carbocyclic Nucleoside Analog
Author(s) -
Bianco Armandodoriano,
Celletti Lucia,
Mazzei Raffaele Antonio,
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(200104)2001:7<1331::aid-ejoc1331>3.0.co;2-m
Subject(s) - chemistry , cyclopentane , nucleoside , stereochemistry , monoterpene , ring (chemistry) , nucleoside analogue , coupling reaction , organic chemistry , catalysis
The synthesis of a new carbocyclic nucleoside starting from aucubin, a natural methylcyclopentanoid monoterpene, has been performed, allowing the preparation of aucubovir II, a carbocyclic nucleoside analog with a highly functionalized cyclopentane ring. The stereocontrol of the coupling reaction was complete, utilizing the procedure described by Vorbrüggen with a purinic base.