title: Iminonitroso Diels-Alder reactions for efficient derivatization and functionalization of complex diene-containing natural products.
abstract: 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.
authors.affiliation: Department of Chemistry and Biochemistry and Walther Cancer Research Center, University of Notre Dame, Notre Dame, Indiana 46556, USA.
authors.forename: Fangzheng
authors.initials: F
authors.lastname: Li
authors.forename: Baiyuan
authors.initials: B
authors.lastname: Yang
authors.forename: Marvin J
authors.initials: MJ
authors.lastname: Miller
authors.forename: Jaroslav
authors.initials: J
authors.lastname: Zajicek
authors.forename: Bruce C
authors.initials: BC
authors.lastname: Noll
authors.forename: Ute
authors.initials: U
authors.lastname: Möllmann
authors.forename: Hans-Martin
authors.initials: HM
authors.lastname: Dahse
authors.forename: Patricia A
authors.initials: PA
authors.lastname: Miller
mesh_terms: 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*
chemical_list: D001688:Biological Products; D007097:Imines; D009603:Nitroso Compounds