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Synthesis Study toward Mayamycin

  1. Kui Wu1,
  2. Meining Wang2,
  3. Qizheng Yao1,*,
  4. Ao Zhang2,*

Article first published online: 8 JAN 2013

DOI: 10.1002/cjoc.201201084

Issue

Chinese Journal of Chemistry

Chinese Journal of Chemistry

Special Issue: Dedicated to the Memory of Professor Wei-Shan Zhou

Volume 31, Issue 1, pages 93–99, January, 2013

Additional Information

How to Cite

Wu, K., Wang, M., Yao, Q. and Zhang, A. (2013), Synthesis Study toward Mayamycin. Chin. J. Chem., 31: 93–99. doi: 10.1002/cjoc.201201084

Author Information

  1. 1

    Department of Medicinal Chemistry, China Pharmaceutical University, Nanjing Jiangsu 210009, China

  2. 2

    Synthetic Organic & Medicinal Chemistry Laboratory, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai 201203, China

*Department of Medicinal Chemistry, China Pharmaceutical University, Nanjing Jiangsu 210009, China

Publication History

  1. Issue published online: 18 JAN 2013
  2. Article first published online: 8 JAN 2013
  3. Manuscript Accepted: 24 DEC 2012
  4. Manuscript Received: 4 NOV 2012

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Keywords:

  • natural product;
  • angucycline;
  • mayamycin;
  • total synthesis;
  • C-glycosilation

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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