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Volumn 64, Issue 5, 1999, Pages 1512-1519

Application of the Tethered Biginelli reaction for enantioselective synthesis of batzelladine alkaloids. Absolute configuration of the tricyclic guanidine portion of batzelladine B

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID; BATZELLADINE; GUANIDINE DERIVATIVE; PYRIMIDINE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 0033525821     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo981971o     Document Type: Article
Times cited : (92)

References (46)
  • 7
    • 0344501258 scopus 로고    scopus 로고
    • note
    • 11 and Snider (Snider, B. B. Personal communication to L.E.O., July 21, 1998) suggest that the stereochemistry of batzelladine F at C4 and C9 is epimeric to that shown in Figure 1.
  • 10
    • 0032491029 scopus 로고    scopus 로고
    • and references to earlier papers from the Murphy group cited therein
    • Black, G. P.; Murphy, P. J.; Walshe, N. D. A. Tetrahedron 1998, 58, 9481 and references to earlier papers from the Murphy group cited therein.
    • (1998) Tetrahedron , vol.58 , pp. 9481
    • Black, G.P.1    Murphy, P.J.2    Walshe, N.D.A.3
  • 31
    • 0001528069 scopus 로고
    • Hydrazoic acid was generated by the procedure reported in: Wolff, H. Org. React. 1946, 3, 327.
    • (1946) Org. React. , vol.3 , pp. 327
    • Wolff, H.1
  • 33
    • 0344501253 scopus 로고    scopus 로고
    • note
    • It should be noted that an insoluble, though labile, intermediate of unknown structure is formed within 1 h when the Biginelli condensation of 24a and allyl acetoacetate was performed in THF. Although this intermediate provided 25b and 26b when reexposed to the reaction conditions in both THF and trifluoroethanol, the diastereoselectivity of the trifluoroethanol reaction dropped below that of the reaction performed in THF.
  • 34
    • 0345363614 scopus 로고    scopus 로고
    • note
    • 37
  • 35
    • 0031584880 scopus 로고    scopus 로고
    • For a recent mechanistic study of the classical Biginelli condensation of aldehydes, β-ketoesters, and urea in the presence of HCl, see: Kappe, C. O.; Fabian, W. M. F.; Semones, M. A. Tetrahedron 1997, 53, 2803.
    • (1997) Tetrahedron , vol.53 , pp. 2803
    • Kappe, C.O.1    Fabian, W.M.F.2    Semones, M.A.3
  • 37
    • 0345363612 scopus 로고    scopus 로고
    • Personal communication to L.E.O., July 19
    • Snider, B. B. Personal communication to L.E.O., July 19, 1996.
    • (1996)
    • Snider, B.B.1
  • 38
    • 0345363613 scopus 로고    scopus 로고
    • note
    • 40
  • 43
    • 0344070081 scopus 로고    scopus 로고
    • note
    • Since the counterion of 10 derived from natural batzelladine A is not described, the significance, if any, of this 30% discrepancy in rotation magnitude is unknown.
  • 44
    • 0344070079 scopus 로고    scopus 로고
    • To be submitted for publication
    • An improved route to the 2a,8a-anti series employing an alternate tethered Biginelli construction of the 4,7-disubstituted-1,2,2a,5,6,7,8,8a-octahydro-5,6,8b-triazaacenaphthylenium-3- carboxylate unit has been developed: Ly, S. K.; Overman, L. E. To be submitted for publication.
    • Ly, S.K.1    Overman, L.E.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.