Ti(iii)-mediated radical cyclization of epoxy-β-aminoacrylate in the synthesis of the substituted pyrrolidine core of necine bases: synthesis of 2-epi-rosmarinecine†
Sandip Basu,Pancham S. Kandiyal,Ravi Sankar Ampapathi,Tushar Kanti Chakraborty
RSC Advances Pub Date : 06/25/2013 00:00:00 , DOI:10.1039/C3RA42315H
Abstract

A radical-mediated approach to the necine base 2-epi-rosmarinecine is described. The synthesis is based on the stereoselective formation of a highly substituted pyrrolidine ring from β-aminoacrylate, diastereoselective allylation and intramolecular cyclization.

Graphical abstract: Ti(iii)-mediated radical cyclization of epoxy-β-aminoacrylate in the synthesis of the substituted pyrrolidine core of necine bases: synthesis of 2-epi-rosmarinecine