RIKEN Advanced Science Institute, 2-1 Hirosawa, Wako, Saitama 351-0198, Japan.
J Am Chem Soc. 2010 Mar 31;132(12):4078-9. doi: 10.1021/ja101280p.
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.
（+）-头抱菌素的全合成首次从已知的 N-Cbz-N-Me-丝氨酸经九步反应完成，其中关键反应为二酮哌嗪 10 的自由基α-溴化反应和 12 的 Co（I）介导的还原二聚反应。对映异构体对头包菌素甲基转移酶（HMT）G9a 的抑制活性相当，但不含硫功能的类似物则无活性。
