THE CYANIDE CATALYZED ISOMERIZATION OF ENOL ESTERS DERIVED FROM CYCLIC 1,3-DIKETONES

Authors
MONTES IF BURGER U
Citation
If. Montes et U. Burger, THE CYANIDE CATALYZED ISOMERIZATION OF ENOL ESTERS DERIVED FROM CYCLIC 1,3-DIKETONES, Tetrahedron letters, 37(7), 1996, pp. 1007-1010
Citations number
21
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
37
Issue
7
Year of publication
1996
Pages
1007 - 1010
Database
ISI
SICI code
0040-4039(1996)37:7<1007:TCCIOE>2.0.ZU;2-G
Abstract
Cross-over experiments unveil that the mechanism of the title reaction consists in cleavage of enol esters by cyanide with transient formati on 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 d erived from pyrrole-2-carboxylic acid to set up the triketide type ske leton 12 of the antibiotic pyoluteorin 16. The aromatization of 12 wit h mercuric acetate gave the pyrrolo[a]indolone 18.