Synthesis of (S)-(-)-N-acetylcolchinol using intramolecular biaryl oxidative coupling

被引：80

作者：

Besong, Gilbert

Jarowicki, Krzysztof

Kocienski, Philip J. ^{[1
]}

Sliwinski, Eric

Boyle, F. Thomas

机构：

[1] Univ Leeds, Sch Chem, Leeds LS2 9JT, W Yorkshire, England

[2] AstraZeneca, Macclesfield SK10 4TG, Cheshire, England

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2006年 / 4卷 / 11期

基金：

英国工程与自然科学研究理事会;

关键词：

D O I：

10.1039/b603857c

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An asymmetric synthesis of the tubulin polymerisation inhibitor ( S)-(-)- N-acetylcolchinol is reported based on an intramolecular biaryl oxidative coupling of a 1,3-diarylpropyl acetamide intermediate using phenyliodonium bis(trifluoroacetate) as the final step. Three syntheses of the penultimate 1,3-diarylpropyl acetamide intermediate ( S)-(-)-N-[1-[3-(tert-butyldimethylsilyloxy) phenyl)]- 3( 3,4,5-trimethoxyphenyl) propyl] acetamide are described which differ in the means by which the stereogenic centre was introduced.

引用

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页码：2193 / 2207

页数：15

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