87. “The cyanide catalyzed isomerization of enol esters derived from cyclic 1,3-diketones”
    Burger, U.; Montes, I. F.
    Tetrahedron Lett. 1996, 37, 1007-1010.

Cross-over experiments unveil that the mechanism of the title reaction consists in cleavage of enol esters by cyanide with transient formation of acyl cyanides. These react as ‘soft’ C-acylating agents with the enolates freed in the initial step. Use is made of the acyl cyanide derived from pyrrole-2-carboxylic acid to set up the triketide type skeleton12 of the antibiotic pyoluteorin 16. The aromatization of 12 with mercuric acetate gave the pyrrolo[a]indolone 18.

DOI : 10.1016/0040-4039(95)02362-3 

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