Myrmicarin alkaloids

Angew. Chem. Int. Ed. Engl. 44, 3668-3688, 2005 Kent, M. and Tepe, J.J., One-pot Friedel-Crafts/ Robinson-Gabriel synthesis of oxazoles using oxazolone templates, J. Org. Chem. 70, 4211 213, 2005 Movassaghi, M. and Ondrus, A.E., Enantioselective total synthesis of tricyclic myrmicarin alkaloids, Org. Lett. 7, 4423 426, 2005 Paizs, C., Katona, A., and Retey, J., The interaction of heteroaryl-acrylates and alanines with phenylalanine ammonia-lyase form parsley. Chemistry 12, 2739-2744, 2006. Cuprous ions have been observed to promote a Friedel-Crafts acylation reaction (Kozikowski, A.P. and Ames, A., Copper(l) promoted acylation reactions. A transition metal-mediated version of the Friedel-Crafts reaction, J. Am. Chem. Soc. 102, 860-862, 1980). 

The decahydrocyclazine skeleton is also found in the alkaloid 395, currently known only by the designation 261C. This compound bears a passing resemblance to some of the myrmicarins (Section 16.6.5.2), but occurs in the skin of a totally different animal species, namely poisonous frogs of the genus Mantella <2003H(59)745>. 

Myrmicarins. Pyrrolo[2,l,5-cd]indolizine alkaloids from the poison gland secretion of the African mtMyr-micaria opaciventris e.g., the monomeric M. 213 B (1) heptacyclic M. 430 A (2), and the most complex... 

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