Bioinspired Total Synthesis of (±)-Yezo'otogirin C
Bioinspired Total Synthesis of (±)-Yezo'otogirin C
复制标题
DOI：
10.1021/ol403374h
复制
发表时间：
2014-01-17
期刊：
影响因子：
5.2
通讯作者：
Lee, Chi-Sing
中科院分区：
文献类型：
--
作者：
He, Shuzhong;Yang, Wei;Lee, Chi-Sing
以3-甲基-4-异戊烯基环己-2-烯酮为起始原料，经八步反应首次实现了（+/-）-yezo'otogirin C的无保护基全合成，总收率23%。（+/-）-yezo'otogirin C的三环核心通过使用Mn（II）/Mn（III）和O-2的生物启发的氧化级联环化策略建立，然后使用硫脲在甲醇中还原过氧桥连的中间体。
The first and protective group-free total synthesis of (+/-)-yezo'otogirin C has been achieved from 3-methyl-4-prenylcyclohex-2-enone in eight steps with 23% overall yield. The tricyclic core of (+/-)-yezo'otogirin C was established via a bioinspired oxidative cascade cyclization strategy using Mn(II)/Mn(III) and O-2, followed by reduction of the peroxy-bridged intermediate using thiourea in refluxing methanol.