期刊
CHEMISTRY-A EUROPEAN JOURNAL
卷 21, 期 16, 页码 6107-6114出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201406286
关键词
cantharimides; cycloadditions; dienes; furans; phthalimide
资金
- GlaxoSmithKline
- Engineering and Physical Sciences Research Council (EPSRC Industrial CASE Award)
- UCL Ph.D. program in Drug Discovery
- Engineering and Physical Sciences Research Council [EP/J01432X/1, 1066970] Funding Source: researchfish
- EPSRC [EP/J01432X/1] Funding Source: UKRI
The [4+2] cycloaddition of 3-alkoxyfurans with N-substituted maleimides provides the first general route for preparing endo-cantharimides. Unlike the corresponding reaction with 3H furans, the reaction can tolerate a broad range of 2-substitued furans including alkyl, aromatic, and heteroaromatic groups. The cycloaddition products were converted into a range of cantharimide products with promising lead-like properties for medicinal chemistry programs. Furthermore, the electron-rich furans are shown to react with a variety of alternative dienophiles to generate 7-oxabicyclo[2.2.1]heptane derivatives under mild conditions. DFT calculations have been performed to rationalize the activation effect of the 3-alkoxy group on a furan Diels-Alder reaction.
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