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4143102008
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note
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Referred to as propargylglycine; 2-amino-5-hexynoic acid is homopropargylglycine, etc.
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31
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Ph. D. Thesis, University of Amsterdam (NL)
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34
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4143108553
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note
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Amino acids 16 and 45 have been synthesized from racemic propargylglycine via esterification followed by N-protection. Racemic propargylglycine is commercially available, but alternatively can be synthesized via alkylation of diethyl acetamidomalonate with propargyl bromide (1.2 equivs.) and NaH (1.1 equivs.), followed by ester and amide hydrolysis with concomitant decarboxylation in 2 M HCl under reflux conditions.
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37
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4143078738
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note
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Crystallographic data (excluding structure factors) of compounds 18 and 47 have been deposited with the Cambridge Crystallographic Data Centre as supplementary publications no. CCDC-203097 (compound 18) and no. CCDC-237704 (compound 47). Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB21EZ, UK [Fax: int. code+ 44(1223)336-033; E-mail: deposit@ccdc.cam.ac.uk].
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For similar Pd-catalyzed coupling cyclization approaches to 2-substituted benzo[b]furans, see: a) W.-M. Dai, K. W. Lai, Tetrahedron Lett. 2002, 43, 9377; b) P. G. Wyatt, M. J. Allen, J. Chilcott, A. Foster, D. G. Livermore, J. E. Mordaunt, J. Scicinski, P. M. Woollard, Bioorg. Med. Chem. Lett. 2002, 12, 1399; c) G. W. Kabalka, L. Wang, R. M. Pagni, Tetrahedron 2001, 57, 8017; d) M. Inoue, M. W. Carson, A. J. Frontier, S. J. Danishefsky, J. Am. Chem. Soc. 2001, 123, 1878.
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0037140886
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For similar Pd-catalyzed coupling cyclization approaches to 2-substituted benzo[b]furans, see: a) W.-M. Dai, K. W. Lai, Tetrahedron Lett. 2002, 43, 9377; b) P. G. Wyatt, M. J. Allen, J. Chilcott, A. Foster, D. G. Livermore, J. E. Mordaunt, J. Scicinski, P. M. Woollard, Bioorg. Med. Chem. Lett. 2002, 12, 1399; c) G. W. Kabalka, L. Wang, R. M. Pagni, Tetrahedron 2001, 57, 8017; d) M. Inoue, M. W. Carson, A. J. Frontier, S. J. Danishefsky, J. Am. Chem. Soc. 2001, 123, 1878.
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41
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0035903909
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For similar Pd-catalyzed coupling cyclization approaches to 2-substituted benzo[b]furans, see: a) W.-M. Dai, K. W. Lai, Tetrahedron Lett. 2002, 43, 9377; b) P. G. Wyatt, M. J. Allen, J. Chilcott, A. Foster, D. G. Livermore, J. E. Mordaunt, J. Scicinski, P. M. Woollard, Bioorg. Med. Chem. Lett. 2002, 12, 1399; c) G. W. Kabalka, L. Wang, R. M. Pagni, Tetrahedron 2001, 57, 8017; d) M. Inoue, M. W. Carson, A. J. Frontier, S. J. Danishefsky, J. Am. Chem. Soc. 2001, 123, 1878.
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Kabalka, G.W.1
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42
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0035819958
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For similar Pd-catalyzed coupling cyclization approaches to 2-substituted benzo[b]furans, see: a) W.-M. Dai, K. W. Lai, Tetrahedron Lett. 2002, 43, 9377; b) P. G. Wyatt, M. J. Allen, J. Chilcott, A. Foster, D. G. Livermore, J. E. Mordaunt, J. Scicinski, P. M. Woollard, Bioorg. Med. Chem. Lett. 2002, 12, 1399; c) G. W. Kabalka, L. Wang, R. M. Pagni, Tetrahedron 2001, 57, 8017; d) M. Inoue, M. W. Carson, A. J. Frontier, S. J. Danishefsky, J. Am. Chem. Soc. 2001, 123, 1878.
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