Oxazolidinone polycyclitols. Stereospecific synthesis of novel aminocarbasugars with oxazolidinone ring

KELEBEKLİ L., Balci N., ŞAHİN E.

TETRAHEDRON, cilt.68, sa.7, ss.1886-1893, 2012 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 68 Sayı: 7
  • Basım Tarihi: 2012
  • Doi Numarası: 10.1016/j.tet.2011.12.078
  • Dergi Adı: TETRAHEDRON
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.1886-1893
  • Atatürk Üniversitesi Adresli: Evet

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.