Journal
TETRAHEDRON
Volume 64, Issue 22, Pages 5200-5207Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2008.03.046
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Cyclotrimerization of beta- or alpha-ethynyl-3,5-di-O-toluoyl-2-deoxy-D-ribofuranose with alpha,omega-diynes proceeded smoothly under Rh-catalysis to afford the corresponding beta- or a-benzene C-nucleoside derivatives. Analogous co-cyclotrimerization of alpha- or beta-propynyl- and -phenylethynyl-3,5-di-O-toluoyl-2-deoxy-D-ribofuranose with alpha,omega-diynes gave the corresponding arene derivatives only under microwave irradiation in the presence of a Rh-catalyst in moderate yields. Attempted homocyclotrimerization of beta- or alpha-ethynyl-3,5-di-O-toluoyl-2-deoxy-D-ribofuranose under Rh-catalysis led only to enynes while the use of Ru-catalyst gave the desired 1,2,4- and 1,3,5-tri-(2-deoxyribofuranose-1-yl)benzene. (c) 2008 Elsevier Ltd. All rights reserved.
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