title: Enantioselective total syntheses of slagenins A-C and their antipodes.
abstract: Full details of the total syntheses of slagenins A-C (1a-c) and their antipodes (2a-c), novel bromopyrrole alkaloids with a unique tetrahydrofuro[2,3-d]imidazolidin-2-one moiety, are described in which their absolute stereochemistry was established. The key step in the syntheses involves the efficient condensation of dihydrofuran-3-one or glyoxal with urea to construct the slagenin bicycle core.
authors.affiliation: State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Road, Shanghai 200032, PR China. jiangb@pub.sioc.ac.cn
authors.forename: Biao
authors.initials: B
authors.lastname: Jiang
authors.forename: Jia-Feng
authors.initials: JF
authors.lastname: Liu
authors.forename: Sheng-Yin
authors.initials: SY
authors.lastname: Zhao
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis*; D000818:Animals; D020650:Combinatorial Chemistry Techniques; D005663:Furans / Q000138:chemical synthesis*; D007093:Imidazoles / Q000138:chemical synthesis*; D007564:Japan; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D011161:Porifera / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000470:Alkaloids; D005663:Furans; D007093:Imidazoles; C416728:slagenin A; C416726:slagenin B; C416727:slagenin C