Stereoselective Synthesis and Biological Evaluation of C1-Epimeric and Desmethyl Monomeric Nuphar Analogues.
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.
Department of Chemistry, Dartmouth College , Hanover, New Hampshire 03755, United States.
Hui
H
Li
Department of Chemistry, Dartmouth College , Hanover, New Hampshire 03755, United States.
Timothy J
TJ
Cooke
Department of Chemistry, Dartmouth College , Hanover, New Hampshire 03755, United States.
Alexander
A
Korotkov
Molecular and Systems Biology, Geisel School of Medicine , Lebanon, New Hampshire 03756, United States.
Charles W
CW
Chapman
Molecular and Systems Biology, Geisel School of Medicine , Lebanon, New Hampshire 03756, United States.
Alan
A
Eastman
Department of Chemistry, Dartmouth College , Hanover, New Hampshire 03755, United States.
Jimmy
0000-0002-0938-8019
J
Wu
D000470:Alkaloids / Q000737:chemistry; D006801:Humans; D031654:Nuphar / Q000737:chemistry*; D013057:Spectrum Analysis / Q000379:methods; D013237:Stereoisomerism; D020298:U937 Cells
D000470:Alkaloids