期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 75, 期 15, 页码 5151-5163出版社
AMER CHEMICAL SOC
DOI: 10.1021/jo100871m
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资金
- CNRS
Synthetic studies toward the spiroketal core of spirangien A are described. Two synthetic approaches were developed. Both of them use a diastereoselective aldol addition of a lithium enolate derived from a methyl ketone on an aldehyde. In the first approach, the introduction of the (E)-trisubstituted terminal olefin was achieved by using an iron-catalyzed cross-coupling between an alkyl iodide and a vinyl Grignard reagent and a randomly protected spiroketal was obtained. In the second approach, a highly functionalized spiroketal carbamate, which includes 13 stereogenic centers, was successfully isolated.
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