Allopumiliotoxin 267A Explained

Allopumiliotoxin 267A is a toxin found in the skin of several poison frogs of the family Dendrobates.^[1] It is a member of the class of compounds known as allopumiliotoxins. The frogs produce the toxin by modifying the original version, pumiliotoxin 251D.^[2] It has been tested on mice and found to be five times more potent than the former version. It has been produced synthetically through a variety of different routes.^{[3] [4] [5] [6]}

See also

• Pumiliotoxin
• Allopumiliotoxin

Notes and References

1. 3236011. 1988. Edwards. M. W.. Alkaloids from a Panamanian poison frog, Dendrobates speciosus: Identification of pumiliotoxin-A and allopumiliotoxin class alkaloids, 3,5-disubstituted indolizidines, 5-substituted 8-methylindolizidines, and a 2-methyl-6-nonyl-4-hydroxypiperidine. Journal of Natural Products. 51. 6. 1188–97. Daly. J. W.. Myers. C. W.. 10.1021/np50060a023.
2. 12960405. 196932. 2003. Daly. J. W.. Evidence for an enantioselective pumiliotoxin 7-hydroxylase in dendrobatid poison frogs of the genus Dendrobates. Proceedings of the National Academy of Sciences of the United States of America. 100. 19. 11092–7. Garraffo. H. M.. Spande. T. F.. Clark. V. C.. Ma. J.. Ziffer. H.. Cover Jr. J. F.. 10.1073/pnas.1834430100. 2003PNAS..10011092D. free.
3. 11428041. 2001. Comins. D. L.. Enantiopure 2,3-dihydro-4-pyridones as synthetic intermediates: A concise asymmetric synthesis of (+)-allopumiliotoxin 267A. Organic Letters. 3. 3. 469–71. Huang. S.. McArdle. C. L.. Ingalls. C. L.. 10.1021/ol0069709.
4. 10.1021/cr950021p . 11848762 . Total Syntheses of Pumiliotoxin a and Allopumiliotoxin Alkaloids. Interplay of Pharmacologically Active Natural Products and New Synthetic Methods and Strategies . Chemical Reviews . 96 . 1 . 505–522 . 1996 . Franklin . Alison S. . Overman . Larry E. .
5. 10.1021/ja001440t . Nickel-Catalyzed Preparation of Bicyclic Heterocycles: Total Synthesis of (+)-Allopumiliotoxin 267A, (+)-Allopumiliotoxin 339A, and (+)-Allopumiliotoxin 339B . Journal of the American Chemical Society . 122 . 29 . 6950–6954 . 2000 . Tang . Xiao-Qing . Montgomery . John .
6. 10.1021/ja00077a044 . Highly stereoselective total syntheses of (+)-allopumiliotoxins 267A and 339A via intramolecular nickel(II)/Chromium(II)-mediated cyclization . Journal of the American Chemical Society . 115 . 24 . 11393–11409 . 1993 . Aoyagi . Sakae . Wang . Tzu Chueh . Kibayashi . Chihiro .