Sundberg indole synthesis applications

Table 1 Early Applications of the Cadogan-Sundberg Indole Synthesis...

Table 2 Applications of the Sundberg Indole Synthesis to Fused Indole Ffeterocycles...

In summary, the exciting applications of Cadogan-Sundberg indole synthesis in the total synthesis of natural products and in drug discovery are a good indication that the reaction may receive more attention in the future. 

An indole alkaloid synthesis employing a bona fide intramolecular Heck reaction was documented in Sundberg s preparation of 5,6-homoiboga derivatives [90]. Several attempts to construct S,6-homoiboga derivative 191 using inter- or intramolecular Heck reaction conditions with phosphine ligands led to poor yields. Application of Jeffery s ligand-free" phase-transfer... 

As the first application of Heck reaction in making heterocyclic compounds — namely indole derivatives, the Mori-Ban reaction has been widely used in variety synthesis of indoles. In a program to synthesize CC-1065 analogs, Sundberg prepared indole 19 from o-bromo-JV-allylaniline 18 in an excellent yield using the Jeffrey s conditions. Silver carbonate and sodium carbonate were less effective than triethylamine. 

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