Synthesis Study toward Mayamycin

Authors

  • Kui Wu,

    1. Department of Medicinal Chemistry, China Pharmaceutical University, Nanjing Jiangsu 210009, China
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  • Meining Wang,

    1. Synthetic Organic & Medicinal Chemistry Laboratory, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai 201203, China
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  • Qizheng Yao,

    Corresponding author
    1. Department of Medicinal Chemistry, China Pharmaceutical University, Nanjing Jiangsu 210009, China
    • Department of Medicinal Chemistry, China Pharmaceutical University, Nanjing Jiangsu 210009, China
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  • Ao Zhang

    Corresponding author
    1. Synthetic Organic & Medicinal Chemistry Laboratory, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai 201203, China
    • Synthetic Organic & Medicinal Chemistry Laboratory, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai 201203, China, Tel.: 0086-021-50806035; Fax: 0086-021-50806035
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Abstract

Natural product mayamycin is the first example in the angucycline class featuring a C-glycoside linkage at the C5-position of the benz[a]anthracenone core with remarkable biological activities. We successfully synthesized the two retrosynthetic fragments, but found that the final C-glycosylation did not occur. Alternatively, an A-ring saturated aglycon was prepared, but the proposed C-glycosylation still did not proceed. Finally, a simplified substrate was used and the subsequent C-glycosylation went through smoothly, giving a two-ring less analogue of mayamycin.

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