jo6b03052_si_001.pdf (8.28 MB)
Stereoselective Synthesis and Biological Evaluation of C1-Epimeric and Desmethyl Monomeric Nuphar Analogues
journal contribution
posted on 2017-02-06, 00:00 authored by Hui Li, Timothy J. Cooke, Alexander Korotkov, Charles W. Chapman, Alan Eastman, Jimmy WuA class of monomeric
nuphar analogues that are either epimeric at C1 and C1′ or
lack the naturally occurring methyl group at those positions were
synthesized and evaluated for biological activity. The syntheses feature
enantioselective vinylogous Mukaiyama–Mannich (vM–Mannich)
reactions catalyzed by chiral phosphoric acids that proceed with excellent
diastereoselectivity. Biological assays reveal that both the desmethyl
and C1-epimeric monomeric nuphar analogous are able to induce rapid
apoptosis.