Azabicycloalkenes as synthetic intermediates: application to the preparation of diazabicycloalkane scaffolds.
[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.
Prenzel
Alexander H G P
AH
Institut für Organische Chemie, Universität Hamburg, Martin-Luther-King-Platz 6, 20146 Hamburg, Germany.
Deppermann
Nina
N
Maison
Wolfgang
W
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
D000473:Alkanes; D000475:Alkenes; D001372:Aza Compounds; D001643:Bridged Bicyclo Compounds; D004151:Dipeptides