First synthesis of 4a-carba-β-D-galactofuranose

The synthesis of 4a-carba-beta-D-galactofuranose is described starting from diacetone glucose. The key ring-closure step was carried out by metathesis to form a cyclopentene. Catalytic hydrogenation of the C=C double bond gave the galacto configured saturated carbahexofuranose with excellent diastereoselectivity. (C) 2007 Elsevier Ltd. All rights reserved.