From lactose towards a novel galactosylated cyclooctenone

Lactose was converted into a disaccharide precursor incorporating an allyl vinyl ether substructure within the glucose residue by vinylation, regioselective silylation, tosylation and subsequent elimination. The thermal Claisen rearrangement led to a novel galactosylated cyclooctenone exhibiting a boat-chair conformation. (C) 2007 Elsevier Ltd. All rights reserved.