期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 79, 期 14, 页码 6759-6764出版社
AMER CHEMICAL SOC
DOI: 10.1021/jo501255c
关键词
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资金
- Australian Research Council
- Institute of Advanced Studies
- CSC Ph.D. scholarship by the Government of the People's Republic of China
The 1,9-ethanoiminomethano-bridged tetrahydrodibenzo[b,d]-furan 2, a non-natural isomer of the alkaloid (-)-galanthamine (1) varying in the manner in which the D-ring is annulated to the ABC-core, has been prepared in racemic form. The synthetic sequence starts with the cyclopropane 3 and involves intramolecular Heck alkenylation and radical-based Smiles rearrangement reactions as key steps. Unlike natural product 1, but as predicted by docking studies, compound 2 is not a potent inhibitor of acetylcholine esterase.
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