Synthesis of trovafloxacin using various (1α, 5α, 6α)-3-azabicyclo [3.1. 0] hexane derivatives

T Norris, TF Braish, M Butters, KM DeVries…

Index: Norris, Timothy; Braish, Tamim F.; Butters, Michael; DeVries, Keith M.; Hawkins, Joel M.; Massett, Stephen S.; Rose, Peter R.; Santafianos, Dinos; Sklavounos, Constantine Journal of the Chemical Society, Perkin Transactions 1, 2000 , # 10 p. 1615 - 1622

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Citation Number: 23

Abstract

Trovafloxacin, a novel broad spectrum antibacterial, contains the unusual (1α, 5α, 6α)-3- azabicyclo [3.1. 0] hexane ring system. The prototype of the industrial synthesis of this ring system and possible mechanistic pathways to exclusive formation of the exo or 6α-nitro derivative 4 are described, which leads to the key 6α-nitro-3-azabicyclo [3.1. 0] hexane intermediate 10. The synthesis of 6α-amino-3-azabicyclo [3.1. 0] hexane 16 and useful ...