Direct, four-step synthetic pathway to iheyamine A and several analogues?

Organic & Biomolecular Chemistry Pub Date: 2022-04-15 DOI: 10.1039/D2OB00397J

Abstract

A novel synthetic route toward the pentacyclic azepinobisindole alkaloid iheyamine A and its several analogues has been developed in four steps from commercially available isatins and tryptamines. This crucial transformation involves the Bischler–Napieralski cyclization to deliver the characteristic seven-membered framework. Then the ester intermediate undergoes a hydrolyzation–decarboxylation–dehydrogenation cascade to yield the final product.

Graphical abstract: Direct, four-step synthetic pathway to iheyamine A and several analogues
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