Total Synthesis of (+)-Chaetocin and its Analogues: Their Histone Methyltransferase G9a Inhibitory Activity
Total Synthesis of (+)-Chaetocin and its Analogues: Their Histone Methyltransferase G9a Inhibitory Activity
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DOI：
10.1021/ja101280p
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发表时间：
2010-03-31
影响因子：
15
通讯作者：
Sodeoka, Mikiko
中科院分区：
文献类型：
--
作者：
Iwasa, Eriko;Hamashima, Yoshitaka;Sodeoka, Mikiko
首次以N-CBZ-N-Me-丝氨酸为原料，以二酮基哌嗪10的自由基α-溴化反应和Co(I)介导的还原二聚反应12为关键反应，经9步反应完成了(+)-毛霉素的首次全合成。这些对映体对组蛋白甲基转移酶(HMT)G9a显示出类似的抑制活性，但没有硫官能团的类似物是无效的。
The first total synthesis of (+)-chaetocin has been accomplished in nine steps starting from known N-Cbz-N-Me-serine using radical alpha-bromination reaction of diketopiperazine 10 and Co(I)-mediated reductive dimerization reaction of 12 as key reactions. The enantiomers show comparable inhibitory activity toward histone methyltransferase (HMT) G9a, but analogues without the sulfur functionality are inactive.