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Multi-component assembly of the bicyclic core associated with the tRNA synthetase inhibitors SB-203207 and SB-203208. Application to the synthesis of biologically active analogues
Authors:Banwell M G  Crasto C F  Easton C J  Karoli T  March D R  Nairn M R  O'Hanlon P J  Oldham M D  Willis A C  Yue W
Institution:Research School of Chemistry, Institute of Advanced Studies, The Australian National University, Canberra, ACT 0200, Australia. mgb@rsc.anu.edu.au
Abstract:The ketone (+/-)-5, which embodies the bicyclic core associated with the title tRNA synthetase inhibitors 1 and 2, has been prepared via a three-component coupling reaction involving 2-(hydroxymethyl)cyclopent-2-enone (15), methylamine (6) and propiolamide (10); straightforward elaboration of the readily derived acetates (-)-21 and (+)-21 has provided the biologically active analogues 23 and 24, respectively, of the title compounds.
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