Intramolecular cationic cyclization of acetoxy derivatives of the levoglucosenone-cyclopentadiene endo-adduct

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 I 2...

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Bibliographic Details
Published in:Russian journal of organic chemistry 2015-04, Vol.51 (4), p.576-581
Main Authors: Biktagirov, I. M., Faizullina, L. Kh, Salikhov, Sh. M., Iskakova, M. M., Safarov, M. G., Galin, F. Z., Valeev, F. A.
Format: Article
Language:English
Subjects:
Chemistry
Chemistry and Materials Science
Organic Chemistry
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Summary: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 I 2 -NaHCO 3 -MeCN gave products resulting from cleavage of the 1,6-anhydro bridge, reduction of the acetal moiety, and olefinaldehyde cyclization.
ISSN:1070-4280
1608-3393
DOI:10.1134/S1070428015040193