PMID: 11325220Apr 28, 2001Paper

Structure of alkaloid 275A, a novel 1-azabicyclo[5.3.0]decane from a dendrobatid frog, Dendrobates lehmanni: synthesis of the tetrahydrodiastereomers

Journal of Natural Products
H M GarraffoV E Zottig

Abstract

The principal alkaloid 275A in skins of the Colombian poison frog Dendrobates lehmanni has been identified as the pyrrolo[1,2-a]azepane (1), the first occurrence in nature of this "izidine" system. Tetrahydro-1 proved identical to one of the four synthetic diastereomers, 2a--2d, thereby establishing that 1 has the 5Z,10E relative stereochemistry. Alkaloid 1 is often accompanied by other congeners, in particular a 5Z,10Z diastereomer 15, a dihydro analogue 16, and a ketone 17. Such izidines in frogs may arise from dietary ants, as do other classes of izidines.

Citations

May 13, 2009·Journal of Natural Products·John W DalyH Martin Garraffo
May 7, 2004·Proceedings of the National Academy of Sciences of the United States of America·Ralph A SaporitoJohn W Daly
Sep 10, 2003·Proceedings of the National Academy of Sciences of the United States of America·John W DalyJohn F Cover
Oct 17, 2002·Proceedings of the National Academy of Sciences of the United States of America·John W DalyMaureen A Donnelly
Feb 21, 2006·Rapid Communications in Mass Spectrometry : RCM·Yan ZhouPang-Chui Shaw
Oct 29, 2005·Journal of Natural Products·John W DalyH Martin Garraffo
Jan 25, 2007·Journal of Natural Products·Tappey H JonesRoy R Snelling
Mar 28, 2018·Organic Letters·Kenichi MuraiHiromichi Fujioka
Apr 5, 2008·Progress in Lipid Research·Robert E Minto, Brenda J Blacklock
May 27, 2006·Journal of Natural Products·Ren-Wang JiangPaul Pui-Hay But
Dec 28, 2005·Journal of Natural Products·N Rabe AndriamaharavoJohn W Daly

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