Total synthesis of auripyrone B using a non-aldol aldol-cuprate opening process.
Total synthesis of auripyrone B using a non-aldol aldol-cuprate opening process.
复制标题
使用非醇醛醇醛-铜酸酯开环工艺全合成金吡喃酮 B。
DOI：
10.1021/ol100985n
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发表时间：
2010
期刊：
影响因子：
5.2
通讯作者：
Salehi-Rad,Ramin
中科院分区：
文献类型：
--
作者：
Jung,MichaelE;Chaumontet,Manon;Salehi-Rad,Ramin
一个非羟醛羟醛铜酸盐的开环在八个步骤中从环氧醚14生成聚丙酸酯11，作为一个单一的非对映体。8与9的高度立体选择性的羟醛缩合反应由于双立体分化而以高产率和优异的非对映选择性得到羟醛产物7。该化合物用于天然产物金吡喃酮B2的有效合成，仅用20步，总收率8%，从14使用后期螺缩酮化到稳定的半缩酮作为最后的关键步骤。
A non-aldol aldol−cuprate opening generates the polypropionate11from the epoxy ether14in eight steps as a single diastereomer. A highly stereoselective aldol reaction of8with9gives the aldol product7in high yield and excellent diastereoselectivity, due to double stereodifferentiation. This compound was used for an efficient synthesis of the natural product auripyrone B2in only 20 steps and 8% overall yield from14using a late-stage spiroketalization onto a stable hemiketal as the final key step.