Synthesis of a D-Ring Isomer of Galanthamine via a Radical-Based Smiles Rearrangement Reaction

被引：18
|
作者：
Lan, Ping [1 ]
Jackson, Colin J. [1 ]
Banwell, Martin G. [1 ]
Willis, Anthony C. [1 ]
机构：
[1] Australian Natl Univ, Inst Adv Studies, Res Sch Chem, Canberra, ACT 0200, Australia
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2014年 / 79卷 / 14期
基金：
澳大利亚研究理事会;
关键词：
INTRAMOLECULAR HECK REACTION; ALZHEIMERS-DISEASE; ACETYLCHOLINESTERASE INHIBITORS; AMARYLLIDACEAE ALKALOIDS; LEUCOJUM-AESTIVUM; SCALE PROCESS; (-)-GALANTHAMINE; (+/-)-GALANTHAMINE; GALANTAMINE; DERIVATIVES;
D O I：
10.1021/jo501255c
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
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.
引用
收藏
页码：6759 / 6764
页数：6
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