Allopumiliotoxin 267A

Allopumiliotoxin 267A

chembox new
ImageFile=Allopumiliotoxin267A.pngImageSize=240
IUPACName=(7R,8R,8aS)-8-methyl-6- [(2R)-2-methylhexylidene] -1,2,3,5,7,8a-hexahydroindolizine-7,8-diol
OtherNames=
Section1=Chembox Identifiers
CASNo=
PubChem= 5366175
SMILES= CC1(O)C2CCCN2CC(=CC(C)CCCC)C1O
Section2=Chembox Properties
C=16 | H=29 | N=1 | O=2
Appearance=
Density=
MeltingPt=
BoilingPt=
Solubility=
Section3=Chembox Hazards
MainHazards=Highly toxic
FlashPt=
Autoignition=

Allopumiliotoxin 267A is a toxin found in the skin of several poison frogs of the family "Dendrobates". [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] The frogs produce the toxin by modifying the original version, pumiliotoxin 251D. [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] 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. [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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