Palladium-Catalyzed Reactions in the Synthesis of 3- and 4-Substituted Indoles. 2. Total Synthesis of the N-Acetyl Methyl Ester of (+/-)-Claviciptic Acids

Article abstract of DOI:10.1021/ja00248a032

The N-acetyl methyl esters of the (+/-)-claviciptic acids 9 were synthesized in 12 steps in overall 18percent yield from commercially available 2-bromo-6-nitrotoluene.The synthesis involved, as key steps, Pd(II)-catalyzed formation of the indole and seven-membered nitrogen-containing C-ring and Pd(0)-catalyzed introduction of both C-ring side-chain precursors.