Preparation of Stereo-Divergent Compounds from the Natural Product Drupacine Based on Complexity-to-Diversity Strategy

  • Chem Biodivers. 2023 Jun;20(6):e202300263. doi: 10.1002/cbdv.202300263.
Yalin Li  1 ,  Yuxing Cai  1 ,  Xingyu Pan  1 ,  Junyi Dong  1 ,  Yuhang Tan  1 ,  Huiling Zeng  1 ,  Zhanpeng Yu  1 ,  Chen Chen  1 ,  Lingyi Kong  1 ,  Jianguang Luo  1
Affiliations
  • 1. Jiangsu Key Laboratory of Bioactive Natural Product Research, State Key Laboratory of Natural Medicines, Department of Natural Medicinal Chemistry, China Pharmaceutical University, 24 Tong Jia Xiang, Nanjing, 210009, P. R. China.
PMID: 37141509 DOI: 10.1002/cbdv.202300263
Abstract

The Complexity-to-Diversity (CtD) strategy was applied to synthesize a 23-member compound collection from the natural product drupacine, including 21 novel compounds. An unusual benzo [d] cyclopenta [b] azepin skeleton was constructed by Von Braun reaction to cleave C-N bond of drupacine. Moreover, compound 10 has potential cytotoxicity to human colon Cancer cells with low toxicity to the normal human colon mucosal epithelial cell lines.

Keywords
Von Braun reaction; cleavage reactions; complexity-to-diversity; drupacine; ketal hydrolysis.
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