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]
^Edwards, M. W.; Daly, J. W.; Myers, C. W. (1988). "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.
doi:
10.1021/np50060a023.
PMID3236011.
^Comins, D. L.; Huang, S.; McArdle, C. L.; Ingalls, C. L. (2001). "Enantiopure 2,3-dihydro-4-pyridones as synthetic intermediates: A concise asymmetric synthesis of (+)-allopumiliotoxin 267A". Organic Letters. 3 (3): 469–71.
doi:
10.1021/ol0069709.
PMID11428041.
^Franklin, Alison S.; Overman, Larry E. (1996). "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.
doi:
10.1021/cr950021p.
PMID11848762.
^Aoyagi, Sakae; Wang, Tzu Chueh; Kibayashi, Chihiro (1993). "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.
doi:
10.1021/ja00077a044.