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

J Org Chem. 2021 Jun 18;86(12):8527-8537. doi: 10.1021/acs.joc.1c00774. Epub 2021 May 27.

Abstract

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(sp2)-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 ring-opening 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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aminoquinolines
  • Bicyclic Monoterpenes
  • Catalysis
  • Cyclobutanes*
  • Keto Acids
  • Palladium

Substances

  • Aminoquinolines
  • Bicyclic Monoterpenes
  • Cyclobutanes
  • Keto Acids
  • Palladium
  • myrtenal
  • 8-aminoquinoline