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 |
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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 |
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Institution: | Research School of Chemistry, Institute of Advanced Studies, The Australian National University, Canberra, ACT 0200, Australia. mgb@rsc.anu.edu.au |
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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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