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Synthetic studies on the azinothricin family of antitumour antibiotics

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

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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.

Type: Thesis (Doctoral)
Title: Synthetic studies on the azinothricin family of antitumour antibiotics
Identifier: PQ ETD:594519
Open access status: An open access version is available from UCL Discovery
Language: English
Additional information: Thesis digitised by ProQuest.
UCL classification: UCL > Provost and Vice Provost Offices > School of Life and Medical Sciences > Faculty of Life Sciences > UCL School of Pharmacy > SoP Pharmaceutical and Bio Chemistry
URI: http://discovery.ucl.ac.uk/id/eprint/1446467
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