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Note | Regular issue | Vol 53, No. 2, 2000, pp.397-407
Published online, 1st January, 1970
DOI: 10.3987/COM-99-8724
Synthesis of Bridged Head Methyl 3,4-O-(1’,2’-Dimethylcycloheaxane-1’,2’-diyl)-6,7-dideoxy-α-D-mannooct-6-enepyranose-8,2-lactone from D-Mannose

Hammed H. A. M. Hassan*

*Chemistry Department, Faculty of Science, Alexandria University, P.O.426-Ibrahimia, 21321 Alexandria, Egypt


The vicinal diequatorial diol at C-3 and C-4 of (1) was masked as cyclohexane diacetal derivative (2). Selective protection of C-2 as benzyl ether (3a) and Swern oxidation of the primary 6-OH gave the aldehyde derivative (4). Stereoselective Wittig condensation of 4 with Ph3P=CH-CO2Me followed by debenzylation and cyclization afforded the bridged α,β-unsaturated lactone derivative (8) in a moderate overall yield.