An efficient organometallic approach to new carbocyclic nucleoside analogues.
[reaction: see text] A general synthetic approach to monoprotected carbocyclic nucleoside analogues, having the nucleobase attached to a 3-hydroxymethyl-4-trialkylsilyloxymethyl-cyclopent-2-en-1-yl scaffold, was developed. A (racemic) key intermediate was prepared by a cobalt-mediated Pauson-Khand reaction. In the course of the further synthesis, the introduction of the nucleobase was achieved with complete regio- and diastereoselectivity through a palladium-catalyzed allylic substitution.
Velcicky
Juraj
J
Institut für Organische Chemie, Universität zu Köln, Greinstrasse 4 D-50939 Köln, Germany.
Lex
Johann
J
Schmalz
Hans-Günther
HG
D000903:Antibiotics, Antineoplastic / Q000138:chemical synthesis*; D018360:Crystallography, X-Ray; D007202:Indicators and Reagents; D008958:Models, Molecular; D009705:Nucleosides / Q000138:chemical synthesis* / Q000737:chemistry; D009942:Organometallic Compounds / Q000138:chemical synthesis* / Q000737:chemistry
D000903:Antibiotics, Antineoplastic; D007202:Indicators and Reagents; D009705:Nucleosides; D009942:Organometallic Compounds