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Volumn 68, Issue 26, 2003, Pages 10020-10029

Total Syntheses of Variolin B and Deoxyvariolin B1

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; PALLADIUM; SYNTHESIS (CHEMICAL);

EID: 0347623391     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo035332b     Document Type: Article
Times cited : (58)

References (39)
  • 1
    • 0035825071 scopus 로고    scopus 로고
    • Taken in part from the Ph.D. Thesis of David Fernández, University of Barcelona, 2001. A preiminary report of portions of this work was presented in: (a) Álvarez, M.; Fernández, D.; Joule, J. A. Tetrahedron Lett. 2001, 42, 315-317.
    • (2001) Tetrahedron Lett. , vol.42 , pp. 315-317
    • Álvarez, M.1    Fernández, D.2    Joule, J.A.3
  • 5
    • 0035803049 scopus 로고    scopus 로고
    • In the literature, two syntheses of variolin B and two syntheses of deoxyvariolin B, as well as several methods for the construction of the common tricyclic skeleton of these compounds, have also been reported: (a) Anderson, R. J.; Morris, J. C. Tetrahedron Lett. 2001, 42, 8697-8699.
    • (2001) Tetrahedron Lett. , vol.42 , pp. 8697-8699
    • Anderson, R.J.1    Morris, J.C.2
  • 10
    • 0345799614 scopus 로고    scopus 로고
    • note
    • 4 at 100 °C, (e) TFA at reflux, (f) MsOH at 100 °C.
  • 15
    • 0347060913 scopus 로고    scopus 로고
    • note
    • 3 at reflux, (c) dry HCl in benzene with a Dean-Stark separator.
  • 20
    • 0020408669 scopus 로고
    • Merchan, F. L.; Garin, J.; Tejero, T. Synthesis 1982, 984-986. Potts, K. T.; Kuehnling, W. R.; Murphy, P. J. Org. Chem. 1984, 49, 2404-2407.
    • (1982) Synthesis , pp. 984-986
    • Merchan, F.L.1    Garin, J.2    Tejero, T.3
  • 36
    • 0346430690 scopus 로고    scopus 로고
    • note
    • Protection of the 9-amino group was important because the iodination of 12a gave an unidentified iodinated product that decomposed during attempted purification, presumably the result of iodine attack at the primary amine.
  • 38
    • 0347060911 scopus 로고    scopus 로고
    • note
    • Acetamide 20a and amine 20b could be separated by column chromatography. See Experimental Section.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.