Modular synthesis of candidate indole-based insulin mimics by Claisen rearrangement.
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.
Xiong
Xin
X
Department of Chemistry, University of California, Riverside, California 92521, USA.
Pirrung
Michael C
MC
D007211:Indoles / Q000737:chemistry*; D007328:Insulin / Q000138:chemical synthesis* / Q000737:chemistry; D018716:Molecular Mimicry
D007211:Indoles; D007328:Insulin