Oxazolidinone polycyclitols. Stereospecific synthesis of novel aminocarbasugars with oxazolidinone ring
Özet
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.
Atıf için künye
KELEBEKLİ, L., Balci, N., & Şahin, 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
BibTeX
@article{kelebekli2012-66825,
author = {KELEBEKLİ, LATİF and Balci, Neslihan and Şahin, Ertan},
title = {Oxazolidinone polycyclitols. Stereospecific synthesis of novel aminocarbasugars with oxazolidinone ring},
journal = {TETRAHEDRON},
year = {2012},
volume = {68},
number = {7},
pages = {1886--1893},
issn = {0040-4020},
doi = {10.1016/j.tet.2011.12.078},
url = {https://akademik.atauni.edu.tr/yayinlar/66825-oxazolidinone-polycyclitols-stereospecific-synthesis-of-novel-aminocarbasugars}
}