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Synthetic studies on the A83586C/GE3 family of antitumour antibiotics.

Lazarides, L.; (2005) Synthetic studies on the A83586C/GE3 family of antitumour antibiotics. Doctoral thesis , University of London. Green open access

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Abstract

The A83586C/GE3 class of cyclodepsipeptides are a family of antitumour antibiotics whose antitumour properties have been attributed to their ability to inhibit E2F transcription factors. The latter are critical regulators of cellular proliferation that are potentially important new therapeutic targets for the control of proliferative diseases such as cancer. In this thesis, the asymmetric total synthesis of several A83586C/GE3/Verucopeptin analogues is described. Some of these molecules have provided valuable insights into the actual mechanism of antitumour activity for this class. All of these molecules have been built through a chemoselective coupling strategy involving the fully elaborated pyran /V-hydroxybenzotriazole activated ester 47 and the relevant unprotected cyclohexadepsipeptide. The latter were each synthesised through a 2+2+2 -fragment condensation strategy and macrolactamisation was accomplished with HATU. The approach used is exemplified below by our synthesis of the A83586C/GE3 hybrid 257.

Type: Thesis (Doctoral)
Title: Synthetic studies on the A83586C/GE3 family of antitumour antibiotics.
Identifier: PQ ETD:592235
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 > UCL BEAMS > Faculty of Maths and Physical Sciences > Dept of Chemistry
URI: http://discovery.ucl.ac.uk/id/eprint/1444925
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