Total Synthesis of (-)-Fusarisetin A and Reassignment of the Absolute Configuration of Its Natural Counterpart
Total Synthesis of (-)-Fusarisetin A and Reassignment of the Absolute Configuration of Its Natural Counterpart
复制标题
DOI：
10.1021/ja211444m
复制
发表时间：
2012-01-18
影响因子：
15
通讯作者：
Li, Ang
中科院分区：
文献类型：
--
作者：
Deng, Jun;Zhu, Bo;Li, Ang
首次全合成了天然产生的腺泡形态发生抑制因子(+)-fusarisetin A的对映体(-)-fusarisetin A，经过13步反应，重新分配了天然产物的绝对构型。该合成具有Lewis酸促进的分子内饮食-Alder反应、Pd催化的O->；C烯丙基重排、化学选择性瓦克氧化和Dieckmann缩合/半酮化级联反应。
The first total synthesis of (-)-fusarisetin A, the enantiomer of naturally occurring acinar morphogenesis inhibitor (+)-fusarisetin A, was accomplished in 13 steps, leading to the reassignment of the absolute configuration of the natural product. The synthesis featured a Lewis acid-promoted intramolecular Diets-Alder reaction, a Pd-catalyzed O -> C allylic rearrangement, a chemoselective Wacker oxidation, and a Dieckmann condensation/hemiketalization cascade.