Total synthesis of (-)-desoxoprosopinine via the diastereoselective reduction of homochiral2-acyl-N-Boc-oxazolidines

Article abstract of DOI:10.1016/S0040-4039(98)00646-7

(-)-Desoxoprosopinine was synthesised from (R)-phenylglycinol as the chiral source. The three distinct steps used for the construction of the three stereogenic centers of the target were all highly diastereoselective. These steps include a reduction of a homochiral N-Boc-2-acyl oxazolidine and the stereoselectivity of this reaction can be explained by a non chelated model. An original N-debenzylation of the phenyl glycinol appendage was devised in this synthesis.