TETRAHEDRON LETTERS, vol.47, no.39, pp.7031-7035, 2006 (SCI-Expanded)
A new aminocyclitol derived from bicyclo[4.2.0(1,6)]octane was synthesized starting from cyclooctatetraene. Photooxygenation of trans-7,8-diacetoxy-bicyclo[4.2.0]octa-2,4-diene afforded a bicyclic endoperoxide. Reduction of the endoperoxide with thiourea followed by a palladium-catalyzed ionization/cyclization reaction gave an oxazolidinone derivative. Oxidation of the double bond in the oxazolidinone with KNlnO(4) followed by acetylation gave the oxazolidinone-tetraacetate whose exact configuration was determined by X-ray diffraction analysis. Hydrolysis of the oxazolidinone ring and removal of the acetate groups furnished the desired aminocyclitol. (c) 2006 Elsevier Ltd. All rights reserved.