Synthesis and Reaction of Strained Azabicyclic Compounds

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The novel synthetic route of Tebipenem pivoxil (TBPM-PI), an oral carbapenem antibiotic, was developed by the use of 1-azabicyclo[1.1.0]butane (ABB), which is the highly strained bicyclic structure. Further, fluoroquinolone antibiotics (20 compounds) which were readily obtained from ABB, were synthesized. And some compounds exhibited fairly potent activities in comparison with the activities of a clinically used fluoroquinolone, Levofloxacine. 2-Bromomethylpyrrolidine were readily cyclized by n-BuLi and LiNH2 to give the strained compound, 1-azabicyclo[3.1.0]hexane (ABH), and therole of the lithium cation was explained by some examinations in this cyclization. Further, the interesting results of the reaction of ABH with a variety of electrophilic reagents were obtained.