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Volumn 121, Issue 45, 1999, Pages 10648-10649

A strategy for macrocyclic ring closure and functionalization aimed toward split-pool syntheses [12]

Author keywords

[No Author keywords available]

Indexed keywords

MACROCYCLIC COMPOUND;

EID: 0033579147     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja992658m     Document Type: Letter
Times cited : (111)

References (20)
  • 2
    • 0019408557 scopus 로고
    • (b) Erythromycin synthesis including ring-closure studies: Woodward, R. B. et al. J. Am. Chem. Soc. 1981, 103, 3210-3213, 3213-3215, 3215-321.
    • (1981) J. Am. Chem. Soc. , vol.103 , pp. 3210-3213
    • Woodward, R.B.1
  • 6
    • 13044288950 scopus 로고    scopus 로고
    • note
    • In this study, the term "natural product-like compounds" can most easily be related to the enterobactins, natural products having 12-membered rings and three unsaturation units (esters) that stabilize analogous hexagonal conformations.
  • 8
    • 13044272568 scopus 로고    scopus 로고
    • (b) http:// www-schreiber.chem.harvard.edu.
  • 9
    • 13044258659 scopus 로고    scopus 로고
    • (c) http://iccb.med.harvard.edu.
  • 10
    • 0342388131 scopus 로고
    • By decreasing ring strain and transannular interactions, trigonal carbons in cyclization substrates can increase the effective molarities of ring-closing reactions that lead to medium rings, see: Illuminati, G.; Mandolini, L.; Masci, B. J. Am. Chem. Soc. 1974, 96, 1422-1427.
    • (1974) J. Am. Chem. Soc. , vol.96 , pp. 1422-1427
    • Illuminati, G.1    Mandolini, L.2    Masci, B.3
  • 12
    • 0029846989 scopus 로고    scopus 로고
    • For an early application, see: Xu, Z.; Johannes, C. W.; Salman, S. S.; Hoveyda, A. H. J. Am. Chem. Soc. 1996, 118, 10926-10927. For a recent review, see: Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413-4450.
    • (1996) J. Am. Chem. Soc. , vol.118 , pp. 10926-10927
    • Xu, Z.1    Johannes, C.W.2    Salman, S.S.3    Hoveyda, A.H.4
  • 13
    • 0032580376 scopus 로고    scopus 로고
    • For an early application, see: Xu, Z.; Johannes, C. W.; Salman, S. S.; Hoveyda, A. H. J. Am. Chem. Soc. 1996, 118, 10926-10927. For a recent review, see: Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413-4450.
    • (1998) Tetrahedron , vol.54 , pp. 4413-4450
    • Grubbs, R.H.1    Chang, S.2
  • 17
    • 13044251442 scopus 로고    scopus 로고
    • note
    • The cis isomer of 5d was obtained from cis-4-octenedioic acid. The independent syntheses of both double bond isomers of 5d prove unambiguously that the RCM reaction produces only the trans isomer. Nevertheless, NMR analyses suggest that several of the macrocycles exist as conformational isomers (ratios ∼3:1 to 6:1, see Supporting Information).


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