Structure of Alkaloid 275A, a Novel 1-Azabicyclo[5.3.0]decane from a Dendrobatid Frog, Dendrobates lehmanni:  Synthesis of the Tetrahydrodiastereomers

Autor: Garraffo, H. M., Jain, P., Spande, T. F., Daly, J. W., Jones, T. H., Smith, L. J., Zottig, V. E.
Zdroj: Journal of Natural Products; April 27, 2001, Vol. 64 Issue: 4 p421-427, 7p
Abstrakt: 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, 2a2d, 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.
Databáze: Supplemental Index