George, Jonathan Harry; (2007) Synthetic studies on the azinothricin family of antitumour antibiotics. Doctoral thesis , UCL (University College London).

Preview

Text George.Jonathan_thesis.pdf Download (15MB) | Preview

Abstract

A first synthesis of the acyl side chain of azinothricin and a second-generation route to the A83586C side chain is described in this thesis. The successful strategy was based on an asymmetric aldol reaction, a stereoselective Roush-type crotylboration and a Trost asymmetric allylic alkylation reaction to set the stereocentres of the key intermediates 3.95 and 3.5, which were subsequently coupled together to give the side chain fragment 3.105 after 10 further steps. The total synthesis of several A83586C/azinothricin analogues is also described. These hybrid structures have been formed via a chemoselective coupling between the N-hydroxybenzotriazole activated ester of the acyl side chain and the appropriate fully deprotected cyclodepsipeptide hydrochloride salt. The first total syntheses of the natural products azinothricin and kettapeptin have also been achieved by this strategy.

Download activity - last month

Export as JSONXMLCSV

Download activity - last 12 months

Export as CSVJSONXML

Downloads by country - last 12 months

Export as JSONXMLCSV

Archive Staff Only

View Item