메뉴 건너뛰기




Volumn 64, Issue 11, 1999, Pages 4050-4059

Total synthesis of O-methylsterigmatocystin using N-alkylnitrilium salts and carbonyl-alkene interconversion in a new xanthone synthesis

Author keywords

[No Author keywords available]

Indexed keywords

2 METHYLSTERIGMATOCYSTIN; AFLATOXIN B1; LITHIUM DERIVATIVE; N BUTYLLITHIUM; UNCLASSIFIED DRUG; XANTHONE DERIVATIVE;

EID: 0033612197     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo990099w     Document Type: Article
Times cited : (37)

References (67)
  • 15
    • 0343906622 scopus 로고
    • Olah, G. A., Ed.; Interscience Publishers: John Wiley & Sons: New York
    • Ruske, W. In Friedel-Crafts and Related Reactions; Olah, G. A., Ed.; Interscience Publishers: John Wiley & Sons: New York, 1964; pp 383-497.
    • (1964) Friedel-Crafts and Related Reactions , pp. 383-497
    • Ruske, W.1
  • 27
    • 0001659119 scopus 로고
    • Bachman, W. E., Fieser, L. F., Blatt, A. H., Johnson, J. R., Eds.; John Wiley & Sons: New York
    • Spoerri, P. E.; DuBois, A. S. in The Hoesch Synthesis; Bachman, W. E., Fieser, L. F., Blatt, A. H., Johnson, J. R., Eds.; John Wiley & Sons: New York, 1949; pp 388-412.
    • (1949) The Hoesch Synthesis , pp. 388-412
    • Spoerri, P.E.1    DuBois, A.S.2
  • 28
    • 0344240107 scopus 로고    scopus 로고
    • note
    • Aryl anion addition to benzonitriles, benzamides, and Vilsmeier-type benzimidoyl chlorides were similarly unsuccessful.
  • 39
    • 0345102417 scopus 로고
    • Lambert, J. B., Riddell, F. G., Eds.; D. Reidel Publishing Company: Boston
    • Lichter, R. L. In Nitrogen Nuclear Magnetic Resonance Spectroscopy; Lambert, J. B., Riddell, F. G., Eds.; D. Reidel Publishing Company: Boston, 1983; pp 207-244.
    • (1983) Nitrogen Nuclear Magnetic Resonance Spectroscopy , pp. 207-244
    • Lichter, R.L.1
  • 42
    • 0344671541 scopus 로고    scopus 로고
    • note
    • The synthesis of 15 will be described in a future publication.
  • 43
    • 0344671540 scopus 로고    scopus 로고
    • note
    • O-Acylation of the nitrilium species blocks unwanted reactions and enhances electrophilicity. It should be noted that entry 5 was carried out with a 2.5-fold excess of the nucleophile to increase the rate of reaction and the net yield. At 1:1 stoichiometry we found that prolonged exposure of this nitrilium salt, and possibly the imine product 19, to the acidic reaction conditions caused removal of the pivaloate ester and side reactions initiated by that unprotected phenol.
  • 64
    • 0344240102 scopus 로고    scopus 로고
    • note
    • 1H NMR spectral assignments we report for OMST 5 are a correction of the original literature and have been verified by NOE experiments conducted on analogous xanthones.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.