Allopumiliotoxin 267A

Allopumiliotoxin 267A

Names
IUPAC name (7R,8R,8aS)-8-Methyl-6-[(2R)-2-methylhexylidene]-1,2,3,5,7,8a-hexahydroindolizine-7,8-diol
Identifiers
CAS Number	73376-38-2
ChemSpider	4580699
Jmol interactive 3D	Image
PubChem	5470308
InChI InChI=1S/C16H29NO2/c1-4-5-7-12(2)10-13-11-17-9-6-8-14(17)16(3,19)15(13)18/h10,12,14-15,18-19H,4-9,11H2,1-3H3/b13-10+/t12-,14+,15-,16-/m1/s1 Key: LWXKAVPXEDNHLL-VRUXTKGDSA-N InChI=1/C16H29NO2/c1-4-5-7-12(2)10-13-11-17-9-6-8-14(17)16(3,19)15(13)18/h10,12,14-15,18-19H,4-9,11H2,1-3H3/b13-10+/t12-,14+,15-,16-/m1/s1 Key: LWXKAVPXEDNHLL-VRUXTKGDBX
SMILES O[C@@H]1C(=C\[C@H](C)CCCC)\CN2[C@H]([C@]1(O)C)CCC2
Properties
Chemical formula	C16H29NO2
Molar mass	267.41 g·mol^−1
Hazards
Main hazards	Highly toxic
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 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

• Pumiliotoxin
• Allopumiliotoxin

References

1. 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
2. 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
3. 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
4. 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.
5. 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.
6. 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.