期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 84, 期 19, 页码 12508-12519出版社
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.9b02017
关键词
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资金
- MEXT [JP26105726]
- JSPS KAKENHI [JP16K08162, JP16KT0051]
- Platform Project for Supporting Drug Discovery and Life Science Research (BINDS) from AMED [JP19am0101099]
We established a method for installing a methyl group at the beta-position of a butenolide ring. The methylated position is located at the congested ring juncture of a 5,6,5-tricyclic lactone, which is common to neurotrophic seco-prezizaane-type sesquiterpenes. The samarium(II)-mediated conjugate addition of the halomethylsilyl ethers tethered to the proximal hydroxy groups efficiently formed the desired C-C bond. Subsequent fluoride-free Tamao oxidation and Barton-McCombie deoxygenation converted the resultant cyclic silyl ether into the corresponding methyl group.
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