Besong Gilbert, Jarowicki Krzysztof, Kocienski Philip J, Sliwinski Eric, Boyle F Thomas
School of Chemistry, Leeds University, Leeds LS2 9JT, UK.
Org Biomol Chem. 2006 Jun 7;4(11):2193-207. doi: 10.1039/b603857c. Epub 2006 May 2.
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.
报道了基于使用双（三氟乙酸）碘苯作为最后一步，对1,3-二芳基丙基乙酰胺中间体进行分子内联芳基氧化偶联的微管蛋白聚合抑制剂（S）-（-）-N-乙酰基秋水仙醇的不对称合成。描述了倒数第二步的1,3-二芳基丙基乙酰胺中间体（S）-（-）-N-[1-[3-（叔丁基二甲基甲硅烷氧基）苯基)]-3-（3,4,5-三甲氧基苯基）丙基]乙酰胺的三种合成方法，它们在引入手性中心的方式上有所不同。
