A Study of an 8-Aminoquinoline-Directed C(sp2)-H Arylation Reaction on the Route to Chiral Cyclobutane Keto Acids from Myrtenal

This work outlines a synthetic route that can be used to access chiral cyclobutane keto acids with two stereocenters in five steps from the inexpensive terpene myrtenal. Furthermore, the developed route includes an 8-aminoquinoline- directed C(sp(2))-H arylation as one of its key steps, which allows a wide range of aryl and heteroaryl groups to be incorporated into the bicyclic myrtenal scaffold prior to the ozonolysis-based ringo-pening step that furnishes the target cyclobutane keto acids. This synthetic route is expected to find many applications connected to the synthesis of natural product-like compounds and small molecule libraries.

Automated summary

This work describes a synthetic route to access chiral cyclobutane keto acids with two stereocenters from inexpensive terpene myrtenal. The developed route includes a key C(sp(2))-H arylation step and an ozonolysis-based ring-opening step, allowing incorporation of various groups and finding applications in the synthesis of natural product-like compounds and small molecule libraries.