-
3
-
-
0011838270
-
-
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.
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Daly, J.W.1
Garraffo, H.M.2
Spande, T.F.3
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4
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0011838270
-
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Pelletier, S. W., Ed.; Wiley: New York, Chapter 1
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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.
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Daly, J.W.1
Spande, T.F.2
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5
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0028228719
-
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For a discussion of the possibility that the skin alkaloids of dendrobatid frogs may have a dietary origin, see: Daly, J. W.; Secunda, S. I. ; Garraffo, H. M.; Spande, T. F.; Wisnieski, A.; Cover, J. F., Jr. Toxicon 1994, 32, 657.
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Spande, T.F.4
Wisnieski, A.5
Cover Jr., J.F.6
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6
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0027297056
-
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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.
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Andriantsiferana, M.6
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7
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0027409184
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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.
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and references cited therein
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Gusovsky, F.; Padgett, W. L.; Creveling, C. R.; Daly, J. W. Mol. Pharmacol. 1992, 42, 1104, and references cited therein.
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(a) Daly, J. W.; McNeal, E. T.; Overman, L. E.; Ellison, D. H. J. Med. Chem. 1985, 25, 482.
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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.
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This second generation synthesis of pumiliotoxin A has been reported in preliminary form: Overman, L. E.; Sharp, M. J. Tetrahedron Lett. 1988, 29, 901.
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9544256599
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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.
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note
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1H NMR analysis of the crude product.
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34
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0001355592
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This sequence was first worked out during our early structural investigations: Overman, L. E.; McCready, R. J. Tetrahedron Lett. 1982, 23, 2741.
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42
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Daly, J. W.; Secunda, S. I.; Gorraffo, H. M.; Spande, T. F.; Wisnieski, A.; Nishihiva, C.; Cover, J. F. Toxicon 1992, 30, 887.
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Cover, J.F.7
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44
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10244254188
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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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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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