title: Azabicycloalkenes as synthetic intermediates: application to the preparation of diazabicycloalkane scaffolds.
abstract: [reaction: see text] A general method to synthesize bicyclic dipeptide mimetics is reported. Key intermediates are azabicycloalkenes 9 and 17, which are prepared via Diels-Alder reactions and subsequent mild deprotection. These unsaturated bicyclic heterocycles are versatile intermediates for different dipeptide mimetics of the aza- and diazabicycloalkane type, which is demonstrated by the synthesis of diazabicycloalkanes 11 and 19 in only 3-6 steps and good overall yield.
authors.affiliation: Institut für Organische Chemie, Universität Hamburg, Martin-Luther-King-Platz 6, 20146 Hamburg, Germany.
authors.forename: Alexander H G P
authors.initials: AH
authors.lastname: Prenzel
authors.forename: Nina
authors.initials: N
authors.lastname: Deppermann
authors.forename: Wolfgang
authors.initials: W
authors.lastname: Maison
mesh_terms: D000473:Alkanes / Q000138:chemical synthesis; D000475:Alkenes / Q000737:chemistry*; D001372:Aza Compounds / Q000138:chemical synthesis* / Q000737:chemistry*; D001643:Bridged Bicyclo Compounds / Q000138:chemical synthesis* / Q000737:chemistry*; D004151:Dipeptides / Q000138:chemical synthesis* / Q000737:chemistry; D018716:Molecular Mimicry; D015394:Molecular Structure
chemical_list: D000473:Alkanes; D000475:Alkenes; D001372:Aza Compounds; D001643:Bridged Bicyclo Compounds; D004151:Dipeptides