Exploration of cascade cyclizations terminated by tandem aromatic substitution: total synthesis of (+)-schweinfurthin A.

Exploration of cascade cyclizations terminated by tandem aromatic substitution: total synthesis of (+)-schweinfurthin A.
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通过串联芳族取代终止级联环化的探索:( )-schweinfurthin A 的全合成。

DOI:
10.1021/jo1022102
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发表时间:
2011
期刊:
The Journal of organic chemistry
影响因子:
--
通讯作者:
Wiemer,DavidF
Wiemer,DavidF
中科院分区:
--
文献类型:
--
作者:
Topczewski,JosephJ;Kodet,JohnG;Wiemer,DavidF

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终止环氧化物引发的级联环化与一系列的“保护”酚类。当保护基可以作为稳定的亲电试剂失去时,级联过程继续超过闭环,以提供已经经历串联亲电芳族取代的产物。许多基团已被证明在这一过程中是可行的,并研究了它们的取代反应的区域化学。该方法首次应用于抗肿瘤药物(+)-schweinfurthin A的全合成。
The termination of epoxide-initiated cascade cyclizations with a range of “protected” phenols is described. When the protecting group can be lost as a stabilized electrophile, the cascade process continues beyond ring closure to afford products which have undergone a tandem electrophilic aromatic substitution. A number of groups have proven viable in this process and the regiochemistry of their substitution reactions has been studied. Application of this methodology in the first total synthesis of (+)-schweinfurthin A, a potent antiproliferative agent, has been achieved.
印度的药用和芳香植物
DOI: --
发表时间: 2008
期刊:
影响因子: --
作者:
S. Maiti;K. Geetha
通讯作者: K. Geetha