Azabicycloalkenes as synthetic intermediates: application to the preparation of diazabicycloalkane scaffolds |
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Authors: | Prenzel Alexander H G P Deppermann Nina Maison Wolfgang |
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Institution: | Institut für Organische Chemie, Universit?t Hamburg, Martin-Luther-King-Platz 6, 20146 Hamburg, Germany. |
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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. |
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