title: Synthesis of bridged diketopiperazines by using the persistent radical effect and a formal synthesis of bicyclomycin.
abstract: A conceptually new and unified approach to diverse bridged diketopiperazines (DKPs) with widely variable ring sizes was developed by taking advantage of the persistent radical effect. This method enables synthesis of the core structures of bridged DKP alkaloids and was applied to a formal synthesis of the antibiotic bicyclomycin.
authors.affiliation: Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, Flemingovo náměstí 2, 16610 Prague (Czech Republic).
authors.forename: Tynchtyk
authors.initials: T
authors.lastname: Amatov
authors.affiliation: Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, Flemingovo náměstí 2, 16610 Prague (Czech Republic).
authors.forename: Radek
authors.initials: R
authors.lastname: Pohl
authors.affiliation: Department of Inorganic Chemistry, Faculty of Science, Charles University in Prague, Hlavova 2030/8, 12843 Prague (Czech Republic).
authors.forename: Ivana
authors.initials: I
authors.lastname: Císařová
authors.affiliation: Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, Flemingovo náměstí 2, 16610 Prague (Czech Republic). jahn@uochb.cas.cz.
authors.forename: Ullrich
authors.initials: U
authors.lastname: Jahn
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis / Q000737:chemistry; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry; D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000138:chemical synthesis / Q000737:chemistry; D018360:Crystallography, X-Ray; D003500:Cyclization; D054659:Diketopiperazines / Q000138:chemical synthesis* / Q000737:chemistry; D008958:Models, Molecular; D013237:Stereoisomerism
chemical_list: D000470:Alkaloids; D000900:Anti-Bacterial Agents; D019086:Bridged Bicyclo Compounds, Heterocyclic; D054659:Diketopiperazines; C024504:bicozamycin
keywords: alkaloids; bicyclomycin; bridged diketopiperazines; cyclization; radicals