메뉴 건너뛰기




Volumn 55, Issue 48, 1999, Pages 13819-13830

Synthesis of a complete series of C-4 fluorinated Phe-Gly mimetics

Author keywords

Aziridines; Fluorine and compounds; Halogenation; Peptide mimetics

Indexed keywords

AZIRIDINE DERIVATIVE; FLUORINE DERIVATIVE; GLYCINE; PHENYLALANINE;

EID: 0033607552     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(99)00865-0     Document Type: Article
Times cited : (22)

References (70)
  • 2
    • 0001834676 scopus 로고    scopus 로고
    • Tetrahedron symposia-in-print number 58: Fluoroorganic chemistry: Synthetic challenges and biomedicinal rewards
    • (b) Tetrahedron Symposia-in-print Number 58: Fluoroorganic Chemistry: Synthetic Challenges and Biomedicinal Rewards Tetrahedron 1996, 52, 1-330.
    • (1996) Tetrahedron , vol.52 , pp. 1-330
  • 3
    • 0014665768 scopus 로고
    • 2. Fluorination in medicinal chemistry, see e.g. (a) Goldman, P. Science 1969, 164, 1123-1130.
    • (1969) Science , vol.164 , pp. 1123-1130
    • Goldman, P.1
  • 5
  • 12
    • 84989585190 scopus 로고
    • and references therein
    • 4. For syntheses of (E)-alkene dipeptide isosteres, see (a) Ibuka, T. J. Synth. Org. Chem. Jpn. 1992, 50, 953-962 and references therein.
    • (1992) J. Synth. Org. Chem. Jpn. , vol.50 , pp. 953-962
    • Ibuka, T.1
  • 24
  • 26
    • 0000420715 scopus 로고
    • 8. For a review on diethylaminosulfur trifluoride (DAST) and its reactions, see Hudlický, M. Org. React. 1988, 35, 513-637.
    • (1988) Org. React. , vol.35 , pp. 513-637
    • Hudlický, M.1
  • 27
    • 33847800447 scopus 로고
    • 9. DAST has been used in fluorinations of alcohols, see e.g. (a) Middleton, W. J. J. Org. Chem. 1975, 40, 574-578.
    • (1975) J. Org. Chem. , vol.40 , pp. 574-578
    • Middleton, W.J.1
  • 37
    • 0029895833 scopus 로고    scopus 로고
    • 10. For a review of difluorination reactions, see Tozer, M. J.; Herpin, T. F. Tetrahedron 1996, 52, 619-8683.
    • (1996) Tetrahedron , vol.52 , pp. 8619-8683
    • Tozer, M.J.1    Herpin, T.F.2
  • 48
    • 0009488155 scopus 로고    scopus 로고
    • 12. With time this conjugated double bond could also be epoxidized. A conjugated double bond reacts slower with electrophilic reagents such as m-CPBA
    • 12. With time this conjugated double bond could also be epoxidized. A conjugated double bond reacts slower with electrophilic reagents such as m-CPBA.
  • 49
    • 0026665555 scopus 로고
    • 13. This type of epoxide ring opening with silica gel has also been observed by others: Wasserman, H. H.; Prowse, K. S. Tetrahedron Lett. 1992, 33, 5423-5426.
    • (1992) Tetrahedron Lett. , vol.33 , pp. 5423-5426
    • Wasserman, H.H.1    Prowse, K.S.2
  • 59
    • 33751386184 scopus 로고
    • 2 has been reported to activate DAST, see McCarthy, J. R.; Peet, N. P.; LeTourneau, M. E.; Inbasekaran, M. J. Am. Chem. Soc. 1985, 107, 735-737.
    • (1993) J. Org. Chem. , vol.58 , pp. 3800-3801
    • Robins, M.J.1    Wnuk, S.F.2
  • 61
    • 0030027447 scopus 로고    scopus 로고
    • 3 to the reaction of 10 from 11 improved the yield from 60% to 83%. However, a corresponding increase in yield was not observed using molecular sieves in the synthesis of 9 from 8. The use of molecular sieves to promote aziridine ring opening reactions has been discussed, see Leung, W.-H.; Yu, M.-T.; Wu, M.-C.; Yeung, L.-L. Tetrahedron Lett. 1996, 37, 891-892.
    • (1996) Tetrahedron Lett. , vol.37 , pp. 891-892
    • Leung, W.-H.1    Yu, M.-T.2    Wu, M.-C.3    Yeung, L.-L.4
  • 62
    • 0009521134 scopus 로고    scopus 로고
    • note
    • N2 reaction from the corresponding alcohol with DAST. Thus, the absolute configuration at C-4 in compound 7 in reference 18 should be inverted.
  • 63
    • 45249128736 scopus 로고
    • and references therein
    • 23. For a review on defluorination by hydrogenolysis, see Hudlický, M. J. Fluorine Chem. 1989, 44, 345-359 and references therein.
    • (1989) J. Fluorine Chem. , vol.44 , pp. 345-359
    • Hudlický, M.1
  • 66
    • 0019968012 scopus 로고
    • Dermorphin
    • 26. Dermorphin: Salvadori, S.; Sarto, G.; Tomatis, R. Int. J. Peptide Protein Res. 1982, 19, 536-542. Substance P: Cascieri, M. A.; Huang, R.-R. C.; Fong, T. M.; Cheung, A. H.; Sadowski, S.; Ber, E.; Strader, C. D. Mol. Pharmacol. 1992, 41, 1096-1099.
    • (1982) Int. J. Peptide Protein Res. , vol.19 , pp. 536-542
    • Salvadori, S.1    Sarto, G.2    Tomatis, R.3
  • 69
    • 0001536689 scopus 로고
    • 28. For other methods to synthesize 6 and 7 see: (a) Hanson, G. J.; Lindberg, T. J. Org. Chem. 1985, 50, 5399-5401.
    • (1985) J. Org. Chem. , vol.50 , pp. 5399-5401
    • Hanson, G.J.1    Lindberg, T.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.