Modular synthesis of candidate indole-based insulin mimics by Claisen rearrangement - PubMed (original) (raw)
. 2008 Mar 20;10(6):1151-4.
doi: 10.1021/ol800058d. Epub 2008 Feb 28.
Affiliations
- PMID: 18303898
- DOI: 10.1021/ol800058d
Modular synthesis of candidate indole-based insulin mimics by Claisen rearrangement
Xin Xiong et al. Org Lett. 2008.
Abstract
A modular synthetic route to (indolyl)kojic acid anti-diabetes agents has been developed. Sonogashira coupling of a protected iodoaniline with a propargyl kojate was used to construct an (indole)methyl kojate. Its heteroaromatic Claisen rearrangement, followed by tautomerization to return the indole and pyrone rings, was used to create the biaryl C-C bond. This route should enable collections of insulin mimic drug candidates to be prepared from a few basic building blocks.
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