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

页码：6759 / 6764

页数：6

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