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Volumn 346, Issue 7, 2004, Pages 823-834

Transition metal-catalyzed synthesis of novel biologically relevant tryptophan analogues

Author keywords

Amino acids; Benzofurans; Catalysis; Homogeneous; Indoles; Isotryptophan; Palladium

Indexed keywords

ACETYLENE; AMINO ACID; BENZOFURAN DERIVATIVE; ENZYME; INDOLE; METAL; METHYL 2 [(TERT BUTOXYCARBONYL)AMINO] 3 (1H 2 INDOLYL)PROPANOATE; METHYL 2 [(TERT BUTOXYCARBONYL)AMINO] 4 (1H 2 INDOLYL)BUTANOATE; METHYL 2 [(TERT BUTOXYCARBONYL)AMINO] 5 (1H 2 INDOLYL)PENTANOATE; METHYL 3 BENZO[B]FURAN 2 YL 2 [[(4 METHYLPHENYL)SULFONYL]AMINO]PROPANOATE; TRANSITION ELEMENT; TRYPTOPHAN DERIVATIVE; UNCLASSIFIED DRUG;

EID: 4143146341     PISSN: 16154150     EISSN: None     Source Type: Journal    
DOI: 10.1002/adsc.200404012     Document Type: Article
Times cited : (57)

References (43)
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    • note
    • Referred to as propargylglycine; 2-amino-5-hexynoic acid is homopropargylglycine, etc.
  • 31
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    • Ph. D. Thesis, University of Amsterdam (NL)
    • a) L. B. Wolf, Ph. D. Thesis, University of Amsterdam (NL), 2001;
    • (2001)
    • Wolf, L.B.1
  • 34
    • 4143108553 scopus 로고    scopus 로고
    • note
    • 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.
  • 37
    • 4143078738 scopus 로고    scopus 로고
    • note
    • 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].
  • 39
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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.
    • (2002) Tetrahedron Lett. , vol.43 , pp. 9377
    • Dai, W.-M.1    Lai, K.W.2
  • 40
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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.
    • (2002) Bioorg. Med. Chem. Lett. , vol.12 , pp. 1399
    • Wyatt, P.G.1    Allen, M.J.2    Chilcott, J.3    Foster, A.4    Livermore, D.G.5    Mordaunt, J.E.6    Scicinski, J.7    Woollard, P.M.8
  • 41
    • 0035903909 scopus 로고    scopus 로고
    • 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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    • 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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    • Inoue, M.1    Carson, M.W.2    Frontier, A.J.3    Danishefsky, S.J.4
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    • For more information, see: www.chiralix.com.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.