Vinyl and alkynyl pyrimidines as michael acceptors: an approach to a cylindrospermopsin substructure.
Vinyl pyrimidine 9 and alkynyl pyrimidine 24 undergo base-mediated intramolecular conjugate addition reactions in which a carbamate and a urea, respectively, behave as nitrogen nucleophiles. The cyclic carbamate derived from 9 was converted to 11 via a metalation-oxidation reaction in which 2-phenylsulfonyl-3-phenyloxaziridine behaves as a hydroxylation reagent. The cyclic urea derived from 24 was converted to cylindrospermopsin substructure 30 using dimethyldioxirane to introduce the C(7) hydroxyl group.
Djung
J F
JF
Department of Chemistry, The Ohio State University, 100 West 18th Avenue, Columbus, Ohio 43210, USA.
Hart
D J
DJ
Young
E R
ER
D000470:Alkaloids; D001427:Bacterial Toxins; D000087522:Cyanobacteria Toxins; D009682:Magnetic Resonance Spectroscopy; D013055:Spectrophotometry, Infrared; D014498:Uracil / Q000031:analogs & derivatives* / Q000737:chemistry
D000470:Alkaloids; D001427:Bacterial Toxins; D000087522:Cyanobacteria Toxins; C089595:cylindrospermopsin; D014498:Uracil