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Volumn 64, Issue 19, 2008, Pages 4332-4346

Diastereoselective synthesis of highly functionalized fluoroalkene dipeptide isosteres and its application to Fmoc-based solid-phase synthesis of a cyclic pentapeptide mimetic

Author keywords

CXCR4 antagonist; Fluoroalkene; Peptide isosteres; Transmetalation

Indexed keywords

9H FLUOREN 9 YLMETHOXY CARBONYL; ALKENE DERIVATIVE; CARBONYL DERIVATIVE; CHEMOKINE RECEPTOR CXCR4 ANTAGONIST; DIPEPTIDE DERIVATIVE; FLUOROALKENE; PENTAPEPTIDE; PEPTIDE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 41549104832     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2008.02.076     Document Type: Article
Times cited : (50)

References (79)
  • 1
    • 0003857670 scopus 로고    scopus 로고
    • Kazmierski W.M. (Ed), Human, Totowa, NJ
    • In: Kazmierski W.M. (Ed). Peptidomimetics Protocols (1999), Human, Totowa, NJ
    • (1999) Peptidomimetics Protocols
  • 5
    • 41549147407 scopus 로고    scopus 로고
    • For some recent examples of (E)-Alkene isostere, see:
    • For some recent examples of (E)-Alkene isostere, see:
  • 9
    • 84894534991 scopus 로고    scopus 로고
    • and references cited therein
    • Badur N.G., Harms K., and Koert U. Synlett (2007) 99-102 and references cited therein
    • (2007) Synlett , pp. 99-102
    • Badur, N.G.1    Harms, K.2    Koert, U.3
  • 10
    • 41549122033 scopus 로고    scopus 로고
    • For the synthesis of 3,6-dihydropyridine-2-one, see:
    • For the synthesis of 3,6-dihydropyridine-2-one, see:
  • 13
    • 41549132707 scopus 로고    scopus 로고
    • For some recent examples of tri- or tetrasubstituted alkene isosteres, see:
    • For some recent examples of tri- or tetrasubstituted alkene isosteres, see:
  • 17
    • 41549149208 scopus 로고    scopus 로고
    • Xaa-Pro type isosteres:
    • Xaa-Pro type isosteres:
  • 19
    • 41549101680 scopus 로고    scopus 로고
    • Fluoroalkene isosteres:
    • Fluoroalkene isosteres:
  • 32
  • 36
    • 41549115969 scopus 로고    scopus 로고
    • 2-mediated reductive defluorination:
    • 2-mediated reductive defluorination:
  • 44
    • 41549146769 scopus 로고    scopus 로고
    • 3Al-copper-mediated alkylative defluorination:
    • 3Al-copper-mediated alkylative defluorination:
  • 50
    • 41549090124 scopus 로고    scopus 로고
    • Copper-mediated reduction of γ-substituted-α,β-enoates:
    • Copper-mediated reduction of γ-substituted-α,β-enoates:
  • 59
    • 41549087102 scopus 로고    scopus 로고
    • note
    • Relatively lower yield observed in the reaction with the higher order cuprate can be partly due to cleavage of chiral auxiliary by a small amount of MeLi remaining in the reaction media.
  • 60
    • 41549106338 scopus 로고    scopus 로고
    • note
    • 12d,14,15
  • 66
    • 41549111629 scopus 로고    scopus 로고
    • note
    • A trace amount of γ-alkylated regioisomer was observed by RP-HPLC.
  • 67
    • 85049057512 scopus 로고
    • HF=35.2-37.8 Hz. These values are consistent with those of compounds possessing (Z)-fluoroolefin units. See:
    • HF=35.2-37.8 Hz. These values are consistent with those of compounds possessing (Z)-fluoroolefin units. See:. Waschüsch R., Carran J., and Savignac P. Tetrahedron 52 (1969) 14199-14216
    • (1969) Tetrahedron , vol.52 , pp. 14199-14216
    • Waschüsch, R.1    Carran, J.2    Savignac, P.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.