Journal
ORGANIC LETTERS
Volume 23, Issue 22, Pages 8843-8846Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.1c03353
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Funding
- National Natural Science Foundation of China [21472077, 21772071]
- Science and Technology Program of Gansu Province [20JR10RA608]
- Fundamental Research Funds for the Central Universities [lzujbky-2021-kb40]
- Department of Education of Guangdong Province [2017KTSCX185, 2017KSYS010, 2019KZDXM035]
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The first total synthesis of (+/-)-furanether A, which demonstrates good antifeedant activity, was achieved in 13 linear steps. The key rigid tetracyclic skeleton containing a 1-methyl-8-oxabicyclo[3.2.1]octane moiety with two vicinal quaternary carbon centers was rapidly constructed in one step through a unique tandem C-H oxidation/oxa-[3,3] Cope rearrangement/aldol cyclization sequence.
The first total synthesis of (+/-)-furanether A, which exhibits good antifeedant activity, has been concisely achieved in 13 linear steps. Notably, the key rigid tetracyclic skeleton containing a 1-methyl-8-oxabicyclo[3.2.1]octane moiety with two vicinal quaternary carbon centers was rapidly constructed in one step through a unique tandem C-H oxidation/oxa-[3,3] Cope rearrangement/aldol cyclization sequence.
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