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Volumn 1, Issue 6, 1999, Pages 913-916

Phorboxazole synthetic studies. 2. Construction of a C(20-28) subtarget, a further extension of the Petasis-Ferrier rearrangement

Author keywords

[No Author keywords available]

Indexed keywords

FUSED HETEROCYCLIC RINGS; OXAZOLE DERIVATIVE; PHORBOXAZOLE A;

EID: 0033598242     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol990829m     Document Type: Article
Times cited : (66)

References (30)
  • 4
    • 0032503570 scopus 로고    scopus 로고
    • For references to other synthetic efforts, see ref 4
    • Forsyth, C. J.; Ahmed, F.; Cink, R. D.; Lee, C. S. J. Am. Chem. Soc. 1998, 120, 5597. For references to other synthetic efforts, see ref 4.
    • (1998) J. Am. Chem. Soc. , vol.120 , pp. 5597
    • Forsyth, C.J.1    Ahmed, F.2    Cink, R.D.3    Lee, C.S.4
  • 8
    • 85034134840 scopus 로고    scopus 로고
    • note
    • 7d
  • 12
    • 85034149699 scopus 로고    scopus 로고
    • note
    • That 12 is not the result of epimerization of the axial methyl group was demonstrated via exposure of 14 to the reaction conditions; no epimerization occurred.
  • 14
    • 85034122337 scopus 로고    scopus 로고
    • note
    • 13C NMR spectra, as well as appropriate ion identification by high-resolution mass spectrometry.
  • 17
    • 85034134225 scopus 로고    scopus 로고
    • note
    • 2O). Large-scale reactions do not proceed until catalytic TfOH (2-4 mol %) is added. Yields and diastereoselectivity were similar with the added TfOH.
  • 20
    • 85034120793 scopus 로고    scopus 로고
    • note
    • 2O/THF) afforded (+)-18 in 97% yield.
  • 27
    • 85034150116 scopus 로고    scopus 로고
    • note
    • The stereochemistry of (+)-16 was secured by NOE experiments and coupling constant analysis.
  • 28
    • 0000693134 scopus 로고
    • For an example of an acetylene stabilizing an oxocarbenium ion in an acetal opening, see: Denmark, S. E.; Almstead, N. G. J. Am. Chem. Soc. 1991, 113, 8089.
    • (1991) J. Am. Chem. Soc. , vol.113 , pp. 8089
    • Denmark, S.E.1    Almstead, N.G.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.