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Total Synthesis of Thaxtomin A and Its Stereoisomers and Findings of Their Biological Activities

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posted on 15.11.2013, 00:00 by Hongbo Zhang, Xin Ning, Hang Hang, Xuyan Ru, Haichen Li, Yonghong Li, Lizhong Wang, Xiao Zhang, Shujing Yu, Yuanyuan Qiao, Xin Wang, Peng George Wang
The first and facile total synthesis of thaxtomin A and its three stereoisomers has been achieved. The synthetic approach involves intramolecular nucleophilic cyclization of an amide toward a ketoamide group to produce a C-hydroxydiketopiperazine scaffold. The most amazing discovery was that each of the four stereoisomers of TA exhibits different phytotoxic, fungicidal, and antiviral activities.

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