Abstract
Epoxidation of diastereoisomeric benzyloxy derivatives of the levoglucosenone adduct with cyclopentadiene by treatment with m-chloroperoxybenzoic acid afforded a mixture of 1,2- and 1,4-epoxy derivatives. Intramolecular cyclization of the hydroxy derivatives of the same adduct by the action of I2-NaHCO3-MeCN gave products resulting from cleavage of the 1,6-anhydro bridge, reduction of the acetal moiety, and olefinaldehyde cyclization.
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Original Russian Text © I.M. Biktagirov, L.Kh. Faizullina, Sh.M. Salikhov, M.M. Iskakova, M.G. Safarov, F.Z. Galin, F.A. Valeev, 2015, published in Zhurnal Organicheskoi Khimii, 2015, Vol. 51, No. 4, pp. 593–598.
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Biktagirov, I.M., Faizullina, L.K., Salikhov, S.M. et al. Intramolecular cationic cyclization of acetoxy derivatives of the levoglucosenone-cyclopentadiene endo-adduct. Russ J Org Chem 51, 576–581 (2015). https://doi.org/10.1134/S1070428015040193
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DOI: https://doi.org/10.1134/S1070428015040193