Iminonitroso Diels-Alder reactions for efficient derivatization and functionalization of complex diene-containing natural products.
A remarkably efficient method for derivatization of complex diene-containing natural products by using stabilized iminonitroso Diels-Alder reactions is described. Turimycin H3, ergosterol, reductiomycin, isoforocidin, colchicine and thebaine were found to react with nitrosopyridines in a highly efficient regio- and stereoselective fashion. Preliminary bioactivity evaluations of turimycin cycloadducts are reported.
Li
Fangzheng
F
Department of Chemistry and Biochemistry and Walther Cancer Research Center, University of Notre Dame, Notre Dame, Indiana 46556, USA.
Yang
Baiyuan
B
Miller
Marvin J
MJ
Zajicek
Jaroslav
J
Noll
Bruce C
BC
Möllmann
Ute
U
Dahse
Hans-Martin
HM
Miller
Patricia A
PA
D001688:Biological Products / Q000737:chemistry*; D018360:Crystallography, X-Ray; D007097:Imines / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D009603:Nitroso Compounds / Q000737:chemistry*
D001688:Biological Products; D007097:Imines; D009603:Nitroso Compounds