An efficient synthesis of the aryl nucleoside analogue 1,2-dideoxy-beta-1-p
henyl-D-ribofuranose (1) is described. This route utilizes the addition of
phenyllithium to a protected 2-deoxyribonolactone followed by reduction wit
h triethylsilane/boron trifluoride etherate to selectively produce the p-an
omer. Deprotection yields the desired aryl C-nucleoside in 27% overall yiel
d from 2-deoxy-D-ribose. (C) 1998 Elsevier Science Ltd. All rights reserved
.