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Volumn 118, Issue 38, 1996, Pages 9062-9072

Efficient total syntheses of pumiliotoxins A and B. Applications of iodide-promoted iminium ion-alkyne cyclizations in alkaloid construction

Author keywords

[No Author keywords available]

Indexed keywords

PUMILIOTOXIN;

EID: 0029827812     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja961641q     Document Type: Article
Times cited : (67)

References (45)
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    • For recent general reviews, see: (a) Daly, J. W.; Garraffo, H. M.; Spande, T. F. Alkaloids 1993, 43, 185. (b) Daly, J. W.; Spande, T. F. In Alkaloids: Chemical and Biological Perspectives; Pelletier, S. W., Ed.; Wiley: New York, 1986; Vol. 4. Chapter 1.
    • (1993) Alkaloids , vol.43 , pp. 185
    • Daly, J.W.1    Garraffo, H.M.2    Spande, T.F.3
  • 4
    • 0011838270 scopus 로고
    • Pelletier, S. W., Ed.; Wiley: New York, Chapter 1
    • For recent general reviews, see: (a) Daly, J. W.; Garraffo, H. M.; Spande, T. F. Alkaloids 1993, 43, 185. (b) Daly, J. W.; Spande, T. F. In Alkaloids: Chemical and Biological Perspectives; Pelletier, S. W., Ed.; Wiley: New York, 1986; Vol. 4. Chapter 1.
    • (1986) Alkaloids: Chemical and Biological Perspectives , vol.4
    • Daly, J.W.1    Spande, T.F.2
  • 6
    • 0027297056 scopus 로고
    • These alkaloids were originally believed to be unique to dendrobatid frogs but recently have been found to have a wide distribution in amphibians: (a) Garraffo, H. M.; Caceres, J.; Daly, J. W.; Spande, T. F.; Andriamaharavo. N. R.; Andriantsiferana, M. J. Nat. Prod. 1993, 56, 1016. (b) Garraffo, H. M.; Spande, T. F. ; Daly, J. W.; Baldessari, A.; Gros, E. G. J. Nat. Prod. 1993, 56, 357.
    • (1993) J. Nat. Prod. , vol.56 , pp. 1016
    • Garraffo, H.M.1    Caceres, J.2    Daly, J.W.3    Spande, T.F.4    Andriamaharavo, N.R.5    Andriantsiferana, M.6
  • 7
    • 0027409184 scopus 로고
    • These alkaloids were originally believed to be unique to dendrobatid frogs but recently have been found to have a wide distribution in amphibians: (a) Garraffo, H. M.; Caceres, J.; Daly, J. W.; Spande, T. F.; Andriamaharavo. N. R.; Andriantsiferana, M. J. Nat. Prod. 1993, 56, 1016. (b) Garraffo, H. M.; Spande, T. F. ; Daly, J. W.; Baldessari, A.; Gros, E. G. J. Nat. Prod. 1993, 56, 357.
    • (1993) J. Nat. Prod. , vol.56 , pp. 357
    • Garraffo, H.M.1    Spande, T.F.2    Daly, J.W.3    Baldessari, A.4    Gros, E.G.5
  • 16
    • 0001098602 scopus 로고    scopus 로고
    • For a recent review of the total synthesis of pumiliotoxin A and allopumiliotoxin alkaloids, see: Franklin, A.; Overman, L. E. Chem. Rev. 1996, 96, 505.
    • (1996) Chem. Rev. , vol.96 , pp. 505
    • Franklin, A.1    Overman, L.E.2
  • 20
    • 0023855168 scopus 로고
    • This second generation synthesis of pumiliotoxin A has been reported in preliminary form: Overman, L. E.; Sharp, M. J. Tetrahedron Lett. 1988, 29, 901.
    • (1988) Tetrahedron Lett. , vol.29 , pp. 901
    • Overman, L.E.1    Sharp, M.J.2
  • 27
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    • We employ pumiliotoxin A numbering for synthetic intermediates in the Results and Discussion. IUPAC names (and numbering) for synthetic intermediates is provided in the Experimental Section. Standard abbreviations we use are defined in J. Org. Chem. 1996, 61, 22A.
    • (1996) J. Org. Chem. , vol.61
  • 31
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    • note
    • 1H NMR analysis of the crude product.
  • 34
    • 0001355592 scopus 로고
    • This sequence was first worked out during our early structural investigations: Overman, L. E.; McCready, R. J. Tetrahedron Lett. 1982, 23, 2741.
    • (1982) Tetrahedron Lett. , vol.23 , pp. 2741
    • Overman, L.E.1    McCready, R.J.2
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    • note
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    • note
    • 2
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    • 10244254188 scopus 로고    scopus 로고
    • Caderas, C.; Lett, R. M.; Overman, L. E.; Rabinowitz, J.; Robinson, L. A., Sharp, M. J.; Zablocki, J., following paper in this issue
    • Caderas, C.; Lett, R. M.; Overman, L. E.; Rabinowitz, J.; Robinson, L. A., Sharp, M. J.; Zablocki, J., following paper in this issue.


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