期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 86, 期 12, 页码 8527-8537出版社
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.1c00774
关键词
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资金
- Wenner-Gren Foundations
- Olle Engkvist Foundation
- Magnus Bergvall foundation
- Wenner-Gren Foundation
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.
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.
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