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 ;
3D model (JSmol)	Interactive image;
ChemSpider	4580699 ;
PubChem CID	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	267.413 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]

References

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. PMID 3236011.
Daly, J. W.; Garraffo, H. M.; Spande, T. F.; Clark, V. C.; Ma, J.; Ziffer, H.; Cover Jr, J. F. (2003). "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. Bibcode:2003PNAS..10011092D. doi:10.1073/pnas.1834430100. PMC 196932. PMID 12960405.
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. PMID 11428041.
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. PMID 11848762.
Tang, Xiao-Qing; Montgomery, John (2000). "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. doi:10.1021/ja001440t.
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.

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[1] 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. PMID 3236011.

[2] Daly, J. W.; Garraffo, H. M.; Spande, T. F.; Clark, V. C.; Ma, J.; Ziffer, H.; Cover Jr, J. F. (2003). "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. Bibcode:2003PNAS..10011092D. doi:10.1073/pnas.1834430100. PMC 196932. PMID 12960405.

[3] 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. PMID 11428041.

[4] 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. PMID 11848762.

[5] Tang, Xiao-Qing; Montgomery, John (2000). "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. doi:10.1021/ja001440t.

[6] 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.

Allopumiliotoxin 267A

See also

References