Allopumiliotoxin 267A
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Allopumiliotoxin 267A
| Allopumiliotoxin 267A | |
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(7R,8R,8aS)-8-Methyl-6-[(2R)-2-methylhexylidene]-1,2,3,5,7,8a-hexahydroindolizine-7,8-diol
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| Identifiers | |
| CAS number | 73376-38-2 |
| PubChem | 5470308 |
| ChemSpider | 4580699  |
| Jmol-3D images | Image 1 |
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SMILES
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| Properties | |
| Molecular formula | C16H29NO2 |
| Molar mass | 267.41 g mol−1 |
| Hazards | |
| Main hazards | Highly toxic |
 267A (verify) (what is:  / ?)Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) |
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| Infobox references | |
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
References
- ^ Edwards MW, Daly JW, Myers CW. 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. 1988 Nov-Dec;51(6):1188-97. PMID 3236011
- ^ Daly JW, Garraffo HM, Spande TF, Clark VC, Ma J, Ziffer H, Cover JF Jr. Evidence for an enantioselective pumiliotoxin 7-hydroxylase in dendrobatid poison frogs of the genus Dendrobates. Proceedings of the National Academy of Sciences USA. 2003 Sep 16;100(19):11092-7. PMID 12960405
- ^ Comins DL, Huang S, McArdle CL, Ingalls CL. Enantiopure 2,3-dihydro-4-pyridones as synthetic intermediates: a concise asymmetric synthesis of (+)-allopumiliotoxin 267A. Organic Letters. 2001 Feb 8;3(3):469-71. PMID 11428041
- ^ Franklin AS, Overman LE. Total Syntheses of Pumiliotoxin A and Allopumiliotoxin Alkaloids. Interplay of Pharmacologically Active Natural Products and New Synthetic Methods and Strategies. Chemical Reviews 1996;96(1),505-522.
- ^ Tang XQ, Montgomery J. Nickel-Catalyzed Preparation of Bicyclic Heterocycles: Total Synthesis of (+)-Allopumiliotoxin 267A, (+)-Allopumiliotoxin 339A, and (+)-Allopumiliotoxin 339B. Journal Of The American Chemical Society. 2000;122(29):6950-6954.
- ^ Aoyagi S, Wang TC, Kibayashi C. Highly stereoselective total syntheses of (+)-allopumiliotoxins 267A and 339A via intramolecular nickel(II)/chromium(II)-mediated cyclization. Journal of the American Chemical Society 1993;115(24):11393-11409.
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