Zhong Jian-Hua, Fishman Alex, Lee-Ruff Edward
Department of Chemistry, York University, 4700 Keele Street, Toronto, Ontario M3J 1P3, Canada.
Org Lett. 2002 Dec 12;4(25):4415-7. doi: 10.1021/ol026881r.
[reaction: see text] A new soluble polymer support synthesis of nucleosides is described. The photochemical ring expansion of cyclobutanones in the presence of poly(ethylene glycol) (PEG) results in polymer-supported ribosides. These photoadducts can be cleaved from the polymer under Vorbrüggen coupling conditions with TMS-protected purines and pyrimidines to give ribonucleosides. The method has been extended to include modified PEGs with dendritic end-groups in order to improve the loading levels for these coupling reactions.
