10.1021/acs.joc.6b03052.s001 Hui Li Hui Li Timothy J. Cooke Timothy J. Cooke Alexander Korotkov Alexander Korotkov Charles W. Chapman Charles W. Chapman Alan Eastman Alan Eastman Jimmy Wu Jimmy Wu Stereoselective Synthesis and Biological Evaluation of C1-Epimeric and Desmethyl Monomeric Nuphar Analogues American Chemical Society 2017 methyl group C 1 lack diastereoselectivity vM Stereoselective Synthesis apoptosi enantioselective chiral phosphoric acids C 1-Epimeric Biological Evaluation monomeric nuphar analogues Desmethyl Monomeric Nuphar Analogues synthese C 1-epimeric monomeric nuphar desmethyl Mukaiyama Biological assays vinylogou 2017-02-06 00:00:00 Journal contribution https://acs.figshare.com/articles/journal_contribution/Stereoselective_Synthesis_and_Biological_Evaluation_of_C1-Epimeric_and_Desmethyl_Monomeric_Nuphar_Analogues/4654309 A 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.