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 language | English (US) |
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Pages (from-to) | 2030-2037 |
Number of pages | 8 |
Journal | European Journal of Organic Chemistry |
Volume | 2015 |
Issue number | 9 |
DOIs | |
State | Published - Mar 2015 |
Externally published | Yes |
Keywords
- Divergent synthesis
- Drug design
- Molecular diversity
- Nitrogen heterocycles
- Organocatalysis
- Spiro compounds
ASJC Scopus subject areas
- Physical and Theoretical Chemistry
- Organic Chemistry