Please use this identifier to cite or link to this item: http://earsiv.odu.edu.tr:8080/xmlui/handle/11489/4299
Title: Oxazolidinone polycyclitols. Stereospecific synthesis of novel aminocarbasugars with oxazolidinone ring
Authors: Kelebekli, Latif
Balci, Neslihan
Sahin, Ertan
Ordu Üniversitesi
Keywords: Oxazolidinone polycyclitol, Oxazolidinone, Aminocarbasugar, Aminocyclitol
AMINOCYCLOPENTITOL GLYCOSIDASE INHIBITORS, CONFORMATIONALLY LOCKED INOSITOLS, VICINAL AMINO-ALCOHOLS, ANTIBACTERIAL ACTIVITY, ALLYLIC ALKYLATIONS, BIOLOGICAL-ACTIVITY, CARBASUGAR HYBRIDS, ORGANIC-CHEMISTRY, NATURAL-PRODUCTS, DERIVATIVES
Issue Date: 2012
Publisher: PERGAMON-ELSEVIER SCIENCE LTD-OXFORD
Citation: Kelebekli, L., Balci, N., Sahin, E. (2012). Oxazolidinone polycyclitols. Stereospecific synthesis of novel aminocarbasugars with oxazolidinone ring. Tetrahedron, 68(7), 1886-1893. https://doi.org/10.1016/j.tet.2011.12.078
Abstract: Two new oxazolidinone polycyclitols, 4,5,7,8,9-pentahydroxy-3-tosyldecahydronaphtho [2,1-d]oxazol-2(9bH)-one and 4,5,6,7,8-pentahydroxy-3-tosyldecahydronaphtho [2,1-d]oxazol-2(9bH)-one were synthesized starting from p-benzoquinone. An endo selective Diels-Alder cycloaddition between p-benzoquinone and 1-acetoxybutadiene followed by stereoselective reduction with NaBH4-CeCl3 center dot 7H(2)O led to the formation of an allylic cis-diol. The obtained diols were protected with p-TsNCO to yield biscarbamates and then a palladium-catalyzed ionization/cyclization reaction produced two oxazolidinone derivatives. Oxidation of the two double bonds in either oxazolidinones with OsO4 followed by acetylation produced oxazolidinone-pentaacetates whose exact configurations were determined by X-ray diffraction analysis. Controlled removal of the acetate groups furnished the desired two new oxazolidinone polycyclitols. (C) 2012 Elsevier Ltd. All rights reserved.
Description: WoS Categories: Chemistry, Organic
Web of Science Index: Science Citation Index Expanded (SCI-EXPANDED); Index Chemicus (IC)
Research Areas: Chemistry
URI: http://dx.doi.org/10.1016/j.tet.2011.12.078
https://www.webofscience.com/wos/woscc/full-record/WOS:000300804400006
http://earsiv.odu.edu.tr:8080/xmlui/handle/11489/4299
ISSN: 0040-4020
Appears in Collections:Kimya

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