Total Synthesis of Trioxacarcins DC-45-A1, A, D, C, and C7″-epi-C and Full Structural Assignment of Trioxacarcin C

Journal of the American Chemical Society
K C NicolaouShugao Zhu

Abstract

Trioxacarcins DC-45-A2, DC-45-A1, A, D, C7″-epi-C, and C have been synthesized through stereoselective strategies involving BF3·Et2O-catalyzed ketone-epoxide opening and gold-catalyzed glycosylation reactions, and the full structural assignment of trioxacacin C was deciphered via the syntheses of both of its C7″ epimers. The gathered knowledge sets the foundation for the design, synthesis, and biological evalution of analogues of these natural products as potential payloads for antibody-drug conjugates and other delivery systems for targeted and personalized cancer chemotherapy.

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Aug 12, 2016·Journal of the American Chemical Society·Yu BaiMingji Dai
Jul 19, 2018·Chemical Communications : Chem Comm·Xu DongLiming Zhang
Sep 20, 2019·Asian Journal of Organic Chemistry·Jesse Ling, Clay S Bennett
Sep 25, 2019·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Zhonglei Wang
Aug 17, 2021·Organic Letters·Renzhi ChenYandong Zhang
Mar 9, 2018·Chemical Reviews·Lei LiYanxing Jia
Jan 4, 2018·Accounts of Chemical Research·Biao Yu
Dec 24, 2018·Accounts of Chemical Research·Kyriacos C Nicolaou, Stephan Rigol
Nov 14, 2020·Journal of the American Chemical Society·K C NicolaouKyoji Tsuchikama

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