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A Study of an 8-Aminoquinoline-Directed C(sp2)–H Arylation Reaction on the Route to Chiral Cyclobutane Keto Acids from Myrtenal
Stockholm University, Faculty of Science, Department of Organic Chemistry.
Stockholm University, Faculty of Science, Department of Organic Chemistry.
Stockholm University, Faculty of Science, Department of Organic Chemistry.
Stockholm University, Faculty of Science, Department of Organic Chemistry. Uppsala University, Sweden.ORCID iD: 0000-0002-3153-748X
Number of Authors: 42021 (English)In: Journal of Organic Chemistry, ISSN 0022-3263, E-ISSN 1520-6904, Vol. 86, no 12, p. 8527-8537Article in journal (Refereed) Published
Abstract [en]

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.

Place, publisher, year, edition, pages
2021. Vol. 86, no 12, p. 8527-8537
National Category
Chemical Sciences
Identifiers
URN: urn:nbn:se:su:diva-196525DOI: 10.1021/acs.joc.1c00774ISI: 000664332300056PubMedID: 34042431OAI: oai:DiVA.org:su-196525DiVA, id: diva2:1591951
Available from: 2021-09-07 Created: 2021-09-07 Last updated: 2022-02-25Bibliographically approved

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Pourghasemi Lati, MonirehStåhle, JonasMeyer, MichaelVerho, Oscar

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