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Hoffmann, R. A wiki for the life sciences where authorship matters. Nature Genetics (2008)

Synthesis of Indoles via 6pi-Electrocyclic Ring Closures of Trienecarbamates.

A new method for the preparation of indoles from readily available alpha-haloenones and alpha-(trialkylstannyl)enecarbamates is described. Following a Stille coupling, trienecarbamate 2 is electronically activated to undergo a facile 6pi-electrocyclic ring closure and subsequent oxidation to afford protected aniline 4. Upon deprotection and reductive amination, acid 5 underwent clean cyclization to N-acetylindole 6 (Ac(2)O, NEt(3), 130 degrees C). This method has been used to construct a variety of substituted indoles that are not easily prepared by conventional indole annelation methods.[1]


  1. Synthesis of Indoles via 6pi-Electrocyclic Ring Closures of Trienecarbamates. Greshock, T.J., Funk, R.L. J. Am. Chem. Soc. (2006) [Pubmed]
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