1316784-90-3Relevant academic research and scientific papers
Synthesis of N,4-diaryl substituted β-lactams via Kinugasa cycloaddition/rearrangement reaction
Michalak, Micha?,Stodulski, MacIej,Stecko, Sebastian,Wo?nica, Magdalena,Staszewska-Krajewska, Olga,Kalicki, Przemys?aw,Furman, Bart?omiej,Frelek, Jadwiga,Chmielewski, Marek
, p. 10806 - 10817 (2013/01/15)
The methodology of construction of N,4-diaryl substituted β-lactam framework, based on the Kinugasa cycloaddition/rearrangement sequence is presented. The series of protected chiral propargyl alcohols was treated with diaryl nitrones to afford mainly the
A formal synthesis of ezetimibe via cycloaddition/rearrangement cascade reaction
Michalak, Michal,Stodulski, MacIej,Stecko, Sebastian,Mames, Adam,Panfil, Irma,Soluch, Magdalena,Furman, Bartlomiej,Chmielewski, Marek
, p. 6931 - 6936 (2011/10/08)
A formal synthesis of a powerful cholesterol inhibitor, ezetymibe 1, is described. The crucial step of the synthesis is based on Cu(I)-mediated Kinugasa cycloaddition/rearrangement cascade reaction between terminal acetylene derived from acetonide of l-glyceraldehyde and suitable C,N-diarylnitrone. The adduct with (3R,4S) configuration at the azetidinone ring, obtained with high stereoselectivity, was subsequently subjected to deprotection of the diol side chain followed by glycolic cleavage and base-induced isomerization at the C3 carbon atom to afford the (3S,4S) aldehyde, which has been already transformed into ezetimibe by the Schering-Plough group.
