Siloxane-based cross-coupling of bromopyridine derivatives: Studies for the synthesis of streptonigrin and lavendamycin
Siloxane-based cross-coupling of bromopyridine derivatives: Studies for the synthesis of streptonigrin and lavendamycin
复制标题
DOI：
10.1021/ol0357503
复制
发表时间：
2003-12-11
期刊：
影响因子：
5.2
通讯作者：
DeShong, P
中科院分区：
文献类型：
--
作者：
McElroy, WT;DeShong, P
制备了高度官能化的4-溴吡啶，发现其与芳基三烷氧基硅烷进行氟化物促进的Pd催化的交叉偶联，得到空间要求高的联芳基。3-硝基-4-溴吡啶衍生物与TBAT（三苯基二氟硅酸四丁基铵）以良好的产率偶联，以提供联芳基加合物，其用作抗肿瘤抗生素链黑菌素和拉文达霉素的全合成的模型系统。
[GRAPHICS]Highly functionalized 4-bromopyridines were prepared and found to undergo fluoride-promoted, Pd-catalyzed cross-coupling with aryltrialkoxysilanes to give sterically demanding biaryls. The 3-nitro-4-bromopyridine derivative coupled in good yield with TBAT (tetrabutylammonium triphenyidifluorosilicate) to provide a biaryl adduct that serves as a model system for the total synthesis of the antitumor antibiotics streptonigrin and lavendamycin.