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

Abstract

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, ¹H NMR, ¹³C NMR, and Elemental Analysis techniques.

Graphical Abstract

Keywords:

• bis-Carbamate
• carbamate
• oxazolidinones
• regioselective