Divergent Cascade Construction of Skeletally Diverse “Privileged” Pyrazole-Derived Molecular Architectures

Yongqiang Zhang, Shanchao Wu, Shengzheng Wang, Kun Fang, Guoqiang Dong, Na Liu, Zhenyuan Miao, Jianzhong Yao, Jian Li, Wannian Zhang, Chunquan Sheng, Wei Wang

Research output: Contribution to journalArticlepeer-review

54 Scopus citations

Abstract

A powerful divergent cascade strategy has been explored for the easy construction of diverse enantioenriched pyrazole-derived scaffolds from readily available chiral fused pyrazole-tetrahydropyran acetals. These versatile intermediates can react in various ways to give Michael–aldol, reduction–lactonization, α-hydroxylation–acetalization–oxidation, and Wittig–aldol and Wittig–oxa-Michael cascade reactions. Using only six simple building blocks, these processes gave five distinct molecular architectures. Furthermore, screening 10 compounds representing the 5 distinct scaffolds revealed potent anticancer lead compounds that deserve further development.

Original languageEnglish (US)
Pages (from-to)2030-2037
Number of pages8
JournalEuropean Journal of Organic Chemistry
Volume2015
Issue number9
DOIs
StatePublished - Mar 2015
Externally publishedYes

Keywords

  • Divergent synthesis
  • Drug design
  • Molecular diversity
  • Nitrogen heterocycles
  • Organocatalysis
  • Spiro compounds

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

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