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

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. A powerful divergent cascade strategy has been developed for the rapid construction of five distinct diverse enantioenriched pyrazole‐derived scaffolds using only six simple building blocks. Furthermore, screening of 10 compounds exemplifying the five synthesized scaffolds revealed potent anticancer lead compounds.