title: Organocatalytic enantioselective formal synthesis of bromopyrrole alkaloids via aza-Michael addition.
abstract: An unprecedented organocatalytic enantioselective formal synthesis of bromopyrrole alkaloid natural products is reported. An organocatalytic aza-Michael addition using pyrroles as the N-centered nucleophile is utilized as the enantioselective step to construct the nitrogen-substituted stereogenic carbon center in bromopyrrole alkaloids in good yield and excellent enantioselectivity. The aza-Michael product is converted via lactamization using a Staudinger-type reductive cyclization to the key intermediate, which was previously used in the total synthesis of bromopyrrole alkaloid natural products.
authors.affiliation: Department of Chemistry, Kyungpook National University, Daegu, Republic of Korea.
authors.forename: Su-Jeong
authors.initials: SJ
authors.lastname: Lee
authors.forename: Seok-Ho
authors.initials: SH
authors.lastname: Youn
authors.forename: Chang-Woo
authors.initials: CW
authors.lastname: Cho
mesh_terms: D000470:Alkaloids / Q000032:analysis / Q000138:chemical synthesis*; D000818:Animals; D000900:Anti-Bacterial Agents / Q000032:analysis / Q000138:chemical synthesis*; D059001:Aquatic Organisms / Q000737:chemistry; D001965:Bromides / Q000737:chemistry; D002384:Catalysis; D002626:Chemistry, Pharmaceutical / Q000379:methods*; D003500:Cyclization; D047029:Lactams, Macrocyclic / Q000737:chemistry; D015394:Molecular Structure; D011161:Porifera / Q000737:chemistry; D011758:Pyrroles / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000470:Alkaloids; D000900:Anti-Bacterial Agents; D001965:Bromides; D047029:Lactams, Macrocyclic; D011758:Pyrroles