A General Synthesis of Substituted Indoles from Cyclic Enol Ethers and Enol Lactones

A general method was developed for the one-pot synthesis of highly functionalized indoles from simple, commercially available aryl hydrazines and cyclic enol ethers. Enol lactones were also used as substrates, affording substituted indole acetic acid or indole propionic acid derivatives. This proced...

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Bibliographic Details
Published in:Organic letters 2004-01, Vol.6 (1), p.79-82
Main Authors: Campos, Kevin R, Woo, Jacqueline C. S, Lee, Sandra, Tillyer, Richard D
Format: Article
Language:English
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Summary:A general method was developed for the one-pot synthesis of highly functionalized indoles from simple, commercially available aryl hydrazines and cyclic enol ethers. Enol lactones were also used as substrates, affording substituted indole acetic acid or indole propionic acid derivatives. This procedure affords 2,3-disubstituted indoles as single regioisomers from the appropriately substituted enol ether or enol lactone. This method was highlighted in the efficient synthesis of the antimigraine drug sumitriptan and the antiinflammatory drug indomethacin.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol036113f