82185-44-2Relevant academic research and scientific papers
ORGANOMETALLIC REAGENTS IN SYNTHESIS A NEW PROTOCOL FOR CONSTRUCTION OF THE INDOLE NUCLEUS
Smith, III, Amos B.,Visnick, Melean,Haseltine, John N.,Sprengeler, Paul A.
, p. 2957 - 2970 (2007/10/02)
Organodilithium reagents derived from 2-alkyl-N-trimethylsilyl anilines undergo condensation with esters of carboxylic acids to afford substituted indoles.A total of 16 examples are reported; yields in general were good.In conjuction with this program, a convenient, large-scale procedure for preparation of monosilylated anilines was also developed.To demonstrate the utility of the new indole protocol in natural products synthesis, efficient syntheses of (+)-cinchonamine and (+)-epi-cinchonamine as well as a tetracyclic model system for the architecturally complex penitrem mycotoxins were completed in regio- and stereoselective fashion.
