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The efficient synthesis of a new class of oxazolidinone with strained rings is described. The allylic  cis -diol as the key intermediate was first prepared  via  two steps starting from  p -benzoquinone. Formation of the  bis -carbamate groups with  p -TsNCO of allylic  cis -diol followed by a Pd(0) catalyzed ionization/cyclization reaction gave the corresponding oxazolidinone derivative. Oxidation and acetylation of only one alkene moiety in the compound gave a diacetate oxazolidinone compound stereoselectively. The structure of diacetate oxazolidinone compound was resolved by X-ray diffraction and the stereochemistry of the structure was determined. Characterization of all the synthesized compounds was performed by FT-IR,  1 H NMR,  13 C NMR, and Elemental Analysis techniques.

Stereospecific synthesis of Pd(0)-catalyzed oxazolidinone with tetracyclic structure