Setup of 4-Prenylated Quinolines through Suzuki-Miyaura Coupling for the Synthesis of Aurachins A and B

A polyprenyl side chain could be introduced into the heterocyclic quinoline moiety through Suzuki-Miyaura coupling of the corresponding quinoline-N-oxide with a polyprenyl boronic acid. This tool could be utilized for the synthesis of the natural product Aurachin B from the myxobacterium Stigmatella aurantiaca. This prenylated quinoline could then be transformed into the related Aurachin A through an epoxidation-ring opening cascade.

Automated summary

A polyprenyl side chain was introduced into the heterocyclic quinoline moiety through Suzuki-Miyaura coupling, enabling the synthesis of Aurachin B from Stigmatella aurantiaca. This prenylated quinoline could then be transformed into the related compound Aurachin A through an epoxidation-ring opening cascade.