Oxazolidinone polycyclitols. Stereospecific synthesis of novel aminocarbasugars with oxazolidinone ring

作者：Kelebekli Latif^*; Balci Neslihan; Sahin Ertan

来源：Tetrahedron, 2012, 68(7): 1886-1893.

DOI：10.1016/j.tet.2011.12.078

• Oxazolidinone polycyclitol
• Oxazolidinone
• Aminocarbasugar
• Aminocyclitol

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.

• 出版日期2012-2-18