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Divergent Cascade Construction of Skeletally Diverse “Privileged” Pyrazole‐Derived Molecular Architectures
Author(s) -
Zhang Yongqiang,
Wu Shanchao,
Wang Shengzheng,
Fang Kun,
Dong Guoqiang,
Liu Na,
Miao Zhenyuan,
Yao Jianzhong,
Li Jian,
Zhang Wannian,
Sheng Chunquan,
Wang Wei
Publication year - 2015
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201403673
Subject(s) - aldol reaction , pyrazole , chemistry , cascade , wittig reaction , combinatorial chemistry , cascade reaction , tetrahydropyran , stereochemistry , organic chemistry , catalysis , ring (chemistry) , chromatography
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.