Abstract
AbstractA modular, efficient, and practical methodology for the preparation of 4‐ and 3‐substituted benzene and aniline C‐ribonucleosides was developed. Addition of 4‐ or 3‐bromophenyllithium (2 or 12) to TBDMS‐protected ribonolactone 3 gave hemiacetal adducts 4 or 13 as pure β‐anomers. Their reduction with Et3SiH and BF3·Et2O afforded the desired protected 4‐ or 3‐bromophenyl‐C‐ribonucleosides 6 or 15 in 66 and 75 %, respectively, over two steps from 3. Bromophenyl intermediates 6 and 15 were subjected to a series of palladium‐catalyzed cross‐coupling, alkoxylation, and amination reactions to give a series of protected 1β‐(3‐ and 4‐substituted phenyl)ribonuleosides 9 and 18. Deprotection of silylated nucleosides 9 or 18 by Et3N·3HF afforded a series of free C‐ribonucleosides 10 or 19 (20 examples). (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)
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