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

Martin G. Banwell; Curtis F. Crasto; Christopher J. Easton; Tomislav Karoli; Darren R. March; Michael R. Nairn; Peter J. O’Hanlon; Mark D. Oldham; Anthony C. Willis; Weimin Yue

doi:10.1039/B104890M

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 analoguesElectronic supplementary information (ESI) available: spectral data for 5, crystal data for (±)-21 (CCDC 165269), HPLC for (+)- and (−)-21. See http://www.rsc.org/suppdata/cc/b1/b104890m/

Martin G. Banwell,*^a Curtis F. Crasto,^a Christopher J. Easton,*^a Tomislav Karoli,^a Darren R. March,^a Michael R. Nairn,^a Peter J. O’Hanlon,^b Mark D. Oldham,^a Anthony C. Willis^a and Weimin Yue^a

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^a Research School of Chemistry, Institute of Advanced Studies, The Australian NationalUniversity, Canberra, Australia.
E-mail: mgb@rsc.anu.edu.au

^b GlaxoSmithKline, New Frontiers Science Park, Harlow, UK

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.

Chemical Communications

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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

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