期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 84, 期 23, 页码 15549-15556出版社
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.9b02532
关键词
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资金
- JSPS KAKENHI [JP17K07779]
We report the first total syntheses of (+)-isolaurenidificin (1) and (-)-bromlaurenidificin (2), the latest acetogenins of the 2,6-dioxabicyclo[3.3.0]octane class. The synthesis features a completely stereoselective one-pot epimerization-ring contraction to establish the cis configuration with respect to C10-H and C12-H of the tetrahydrofuran ring. Six stereogenic centers and an olefin geometry were constructed in a highly stereoselective manner. Absolute configurations of the natural products were deduced by the comparison of NMR data and specific rotations.
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