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Volumn 11, Issue 5, 2009, Pages 1167-1170

Passerini reaction-amine deprotection-acyl migration peptide assembly: Efficient formal synthesis of cyclotheonamide c

Author keywords

[No Author keywords available]

Indexed keywords

AMINE; CYCLOPEPTIDE; CYCLOTHEONAMIDE C; PEPTIDE;

EID: 64349097304     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol900048r     Document Type: Article
Times cited : (48)

References (45)
  • 3
    • 51849085222 scopus 로고    scopus 로고
    • Recent leading articles: (a) Qian, J.; Cuerrier, D.; Davies, P. L.; Li, Z.; Powers, J. C.; Campbell, R. L. J. Med. Chem. 2008, 51, 5264.
    • Recent leading articles: (a) Qian, J.; Cuerrier, D.; Davies, P. L.; Li, Z.; Powers, J. C.; Campbell, R. L. J. Med. Chem. 2008, 51, 5264.
  • 26
    • 26844537872 scopus 로고    scopus 로고
    • Recent reviews: a
    • Recent reviews: (a) Banfi, L.; Riva, R. Org. React. 2005, 65, 1.
    • (2005) Org. React , vol.65 , pp. 1
    • Banfi, L.1    Riva, R.2
  • 33
    • 6444223724 scopus 로고    scopus 로고
    • An interesting related process involving acylcyanides in place of aldehydes has been described: Oaksmith, J. M, Peters, U, Ganem, B. J. Am. Chem. Soc. 2004, 126, 13606
    • An interesting related process involving acylcyanides in place of aldehydes has been described: Oaksmith, J. M.; Peters, U.; Ganem, B. J. Am. Chem. Soc. 2004, 126, 13606.
  • 35
    • 36248957157 scopus 로고    scopus 로고
    • The O, N-acyl migration in an O-acyl isopeptide has been exploited for the synthesis of an amyloid β-peptide, see: Skwarczynski, M.; Kiso, Y. Curr. Med. Chem. 2007, 14, 2813, and references cited therein.
    • The O, N-acyl migration in an O-acyl isopeptide has been exploited for the synthesis of an amyloid β-peptide, see: Skwarczynski, M.; Kiso, Y. Curr. Med. Chem. 2007, 14, 2813, and references cited therein.
  • 41
    • 0142042901 scopus 로고    scopus 로고
    • In related work (unpublished), racemization occurred during the preparation of the ester isonitrile from enantiomerically pure L-N-formyl-Phe-OMe in our hands; for similar problems, see: Bon, R. S.; Hong, C.; Bouma, M. J.; Schmitz, R. F.; De Kanter, F. J. J.; Lutz, M.; Spek, A. L.; Orru, R. V. A. Org. Lett. 2003, 5, 3759. We therefore verified that no such problems arose for amide isonitriles, such as 10a and 10b, using a known model amide isonitrile. See the Supporting Information for details.
    • In related work (unpublished), racemization occurred during the preparation of the ester isonitrile from enantiomerically pure L-N-formyl-Phe-OMe in our hands; for similar problems, see: Bon, R. S.; Hong, C.; Bouma, M. J.; Schmitz, R. F.; De Kanter, F. J. J.; Lutz, M.; Spek, A. L.; Orru, R. V. A. Org. Lett. 2003, 5, 3759. We therefore verified that no such problems arose for amide isonitriles, such as 10a and 10b, using a known model amide isonitrile. See the Supporting Information for details.
  • 44
    • 38049046061 scopus 로고    scopus 로고
    • 1H NMR spectral analysis. Subsequent analysis of product 15, derived from 13c, confirmed that the dr was low (vide infra). For an enantioselective catalytic P-3CR and leading references on diastereoselective P-3CR, see: Wang, S.-X.; Wang, M.-X.; Wang, D.-X.; Zhu, J. Angew. Chem., Int. Ed. 2008, 47, 388.
    • 1H NMR spectral analysis. Subsequent analysis of product 15, derived from 13c, confirmed that the dr was low (vide infra). For an enantioselective catalytic P-3CR and leading references on diastereoselective P-3CR, see: Wang, S.-X.; Wang, M.-X.; Wang, D.-X.; Zhu, J. Angew. Chem., Int. Ed. 2008, 47, 388.
  • 45
    • 64349107956 scopus 로고    scopus 로고
    • This transformation proved to be difficult to monitor by TLC (identical Rf values) and 1H NMR presence of diastereoisomers and rotamers
    • 1H NMR (presence of diastereoisomers and rotamers).


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