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Volumn 118, Issue 40, 1996, Pages 9606-9614

Application of ring-closing metathesis to the synthesis of rigidified amino acids and peptides

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOPEPTIDE;

EID: 0029860486     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja961626l     Document Type: Article
Times cited : (479)

References (73)
  • 1
    • 0001270989 scopus 로고
    • Trost, B. M., Ed.; Pergamon: New York, Chapter 9.3
    • For a recent reviews on applications of olefin metathesis and related processes in organic synthesis, see: (a) Grubbs, R. H.; Pine, S. H. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon: New York, 1991; Vol. 5, Chapter 9.3.
    • (1991) Comprehensive Organic Synthesis , vol.5
    • Grubbs, R.H.1    Pine, S.H.2
  • 4
    • 0001263185 scopus 로고
    • For previous reports on RCM from this laboratory, see: (a) Fu, G. C.; Grubbs, R. H. J. Am. Chem. Soc. 1992, 114, 5426-5427.
    • (1992) J. Am. Chem. Soc. , vol.114 , pp. 5426-5427
    • Fu, G.C.1    Grubbs, R.H.2
  • 18
    • 0028013298 scopus 로고
    • For recent applications of metathesis-based methods to natural product synthesis, see: (a) Martin, S. F.; Liao, Y.; Rein, T. Tetrahedron Lett. 199-4, 35, 691-694.
    • (1994) Tetrahedron Lett. , vol.35 , pp. 691-694
    • Martin, S.F.1    Liao, Y.2    Rein, T.3
  • 38
    • 33847488366 scopus 로고    scopus 로고
    • 13C NMR, IR, and mass spectral characteristics (see Experimetal Section). The cases involving C-allylglycine in Scheme 1 were performed on the racemic mixtures
    • 13C NMR, IR, and mass spectral characteristics (see Experimetal Section). The cases involving C-allylglycine in Scheme 1 were performed on the racemic mixtures.
  • 39
    • 33847474941 scopus 로고    scopus 로고
    • We have discussed this issue in more detail in ref 2g
    • We have discussed this issue in more detail in ref 2g.
  • 40
    • 0001653694 scopus 로고
    • Vinyl glycine derivative 8 was prepared by derivatization of N-allylN-BOC-methionine methyl ester in analogy to the procedure of Rapoport, see: (a) Afzali-Ardakani, A.; Rapoport, H. J. Org. Chem. 1980, 45, 4817-4820.
    • (1980) J. Org. Chem. , vol.45 , pp. 4817-4820
    • Afzali-Ardakani, A.1    Rapoport, H.2
  • 42
    • 33646951660 scopus 로고    scopus 로고
    • note
    • A monocyclized product was identified by FABMS. No ions corresponding to the bicyclization product could be detected. The monocyclized product was formed at approximately the same rate as the six-membered cyclic product 5, and no other product was formed after elongated reaction time. The formation of cyclic product 5 was previously found to be fast and effectively irreversible. Thus, we believe that treatment of substrate 10 under the analogous reaction conditions leads to the sixmembered monocyclization product as opposed to the 11-membered monocyclization product.
  • 46
    • 0021779081 scopus 로고
    • For a review of β-turn mimetics, see: ref 7b
    • (b) Rose, G. D.; Gierasch, L. M.; Smith, J. A. Adv. Protein Chem. 1985, 37, 1-109. For a review of β-turn mimetics, see: ref 7b.
    • (1985) Adv. Protein Chem. , vol.37 , pp. 1-109
    • Rose, G.D.1    Gierasch, L.M.2    Smith, J.A.3
  • 50
    • 0000644502 scopus 로고
    • The disulfide dihedral angle in 10 has been shown to be 82° with right-handed chirality in the solid state. Ravi. A.; Prasad, B. V.; Balaram, P. J. Am. Chem. Soc. 1983, 105, 105-109.
    • (1983) J. Am. Chem. Soc. , vol.105 , pp. 105-109
    • Ravi, A.1    Prasad, B.V.2    Balaram, P.3
  • 53
    • 33847487057 scopus 로고    scopus 로고
    • A related cyclization was performed with unprotected tyrosine which afforded the analogous macrocycle in 70% yield. The free phenol therefore does not interfere with catalyst activity
    • A related cyclization was performed with unprotected tyrosine which afforded the analogous macrocycle in 70% yield. The free phenol therefore does not interfere with catalyst activity.
  • 58
    • 33847464392 scopus 로고    scopus 로고
    • See ref 19
    • See ref 19.
  • 59
    • 33847460682 scopus 로고    scopus 로고
    • See ref 18
    • See ref 18.
  • 60
    • 33847454208 scopus 로고    scopus 로고
    • The olefin geometry of 22 was not assigned
    • The olefin geometry of 22 was not assigned.
  • 61
    • 77956767815 scopus 로고
    • For literature on cyclization reactions performed on solid-supportbound substrates, see: (a) Hiroshige, M.; Hauske, J. R.; Zhou, P. J. Am. Chem. Soc. 1995, 117, 11590-11591.
    • (1995) J. Am. Chem. Soc. , vol.117 , pp. 11590-11591
    • Hiroshige, M.1    Hauske, J.R.2    Zhou, P.3
  • 69
    • 33847478974 scopus 로고    scopus 로고
    • See ref 3
    • See ref 3.
  • 70
    • 0004266860 scopus 로고
    • Springer-Verlag: New York, and references therein
    • Bodansky, M. Peptide Chemistry; Springer-Verlag: New York, 1988, pp 55-146 and references therein.
    • (1988) Peptide Chemistry , pp. 55-146
    • Bodansky, M.1
  • 71
    • 33847453823 scopus 로고    scopus 로고
    • 1H NMR. This impurity is not present in the cyclized product 16
    • 1H NMR. This impurity is not present in the cyclized product 16.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.