Premium
A New Modular and Practical Methodology for the Synthesis of 4‐ or 3‐Substituted Phenyl C‐Nucleosides
Author(s) -
Hocek Michal,
Pohl Radek,
Klepetářová Blanka
Publication year - 2005
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/ejoc.200500607
Subject(s) - chemistry , epimer , nucleoside , combinatorial chemistry , modular design , coupling reaction , nucleic acid , stereochemistry , organic chemistry , catalysis , biochemistry , computer science , operating system
A novel efficient and practical approach to the synthesis of 4‐ or 3‐substituted phenyl C‐nucleosides has been developed. It consists in coupling of protected halogenose 1 with bromophenylmagnesium bromides followed by acid mediated epimerization to prepare 4‐ or 3‐bromophenyl C‐nucleoside intermediates. Their Pd‐catalyzed cross‐coupling reactions with diverse organometallics followed by deprotection afforded the title nucleoside analogues. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)