Total Synthesis of (+)-Chaetocin and its Analogues: Their Histone Methyltransferase G9a Inhibitory Activity
Journal of the American Chemical Society2010Vol. 132(12), pp. 4078–4079
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Eriko Iwasa, Yoshitaka Hamashima, Shinya Fujishiro, Eisuke Higuchi, Akihiro Ito, Minoru Yoshida, Mikiko Sodeoka
Abstract
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.
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