Open AccessA Study of an 8-Aminoquinoline-Directed C(sp2)–H Arylation Reaction on the Route to Chiral Cyclobutane Keto Acids from Myrtenal
Author(s) -
Monireh Pourghasemi Lati,
Jonas Ståhle,
Michelle M. Meyer,
Oscar Verho
Publication year - 2021
Publication title -
journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.2
H-Index - 228
eISSN - 1520-6904
pISSN - 0022-3263
DOI - 10.1021/acs.joc.1c00774
Subject(s) - cyclobutane , chemistry , stereocenter , bicyclic molecule , ring (chemistry) , ozonolysis , aryl , chemical space , stereochemistry , ether , lactone , terpene , molecule , combinatorial chemistry , enantioselective synthesis , organic chemistry , catalysis , drug discovery , alkyl , biochemistry
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 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.