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Journal of the American Chemical Society

Total synthesis of (+)-chaetocin and its analogues: their histone methyltransferase G9a inhibitory activity.


PMID 20210309

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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