175891-54-0Relevant academic research and scientific papers
Stereoselective synthesis of a key intermediate of sanfetrinem by means of a chelated tin(IV) enolate
Rossi, Tino,Marchioro, Carla,Paio, Alfrede,Thomas, Russell J.,Zarantonello, Paola
, p. 1653 - 1661 (2007/10/03)
(2S)-2-Methoxycyclohexanone [(2S)-6], reacts with the 4-acetoxyazetidinone 3a in the presence of SnCl4 and a tertiary amine base (such as N,N-diisopropylethylamine) to give the ketoazetidinone 5 (a key intermediate in the synthesis of the broad
A highly stereoselective and practical total synthesis of the tricyclic β-lactam antibiotic GV104326 (4-methoxytrinem)
Hanessian, Stephen,Rozema, Michael J.
, p. 9884 - 9891 (2007/10/03)
A novel and practical total synthesis of a tricyclic β-lactam antibiotic, GV104326 (4-methoxytrinem or Sanfetrinem) has been achieved in nine steps and about 33% overall yield from a commercially available acetoxyazetidinone chiron. A key step in the high
The use of zinc enolates in the synthesis of a key intermediate for the preparation of trinem antibiotics
Kennedy, Gordon,Rossi, Tino,Tamburini, Bruno
, p. 7441 - 7444 (2007/10/03)
The stereoselective preparation of 2a, a key intermediate in the synthesis of the broad spectrum tricyclic β-lactam antibiotic GV104326 1, by the reaction of a zinc enolate derived from chiral non-racemic 2-methoxycyclohexanone with azetidinone 3 is described.
Synthesis and antibacterial activity of 4- and 8-methoxy trinems
Andreotti, Daniele,Rossi, Tino,Gaviraghi, Giovanni,Donati, Daniele,Marchioro, Carla,Di Modugno, Enza,Perboni, Alcide
, p. 491 - 496 (2007/10/03)
The synthesis of all the isomers of 8-methoxy-(9S,10S,12R)-10-(1-hydroxyethyl)-11-oxo-1-azatricyclo-[7.20. 03,8]-undec-2-ene-carboxylates 2 and 4-methoxy-(9R,10S,12R)-10-(1-hydroxyethyl)-11-oxo-1-azatricyclo-[7.2.0 .03,8]-undec-2-ene
The stereoselective synthesis of a key intermediate of the trinem antibiotic Sanfetrinem
Ghiron, Chiara,Piga, Elisabetta,Rossi, Tino,Tamburini, Bruno,Thomas, Russell J.
, p. 3891 - 3894 (2007/10/03)
By modulating the reactivity of the Lewis acid promoter it was possible to obtain, in a single stereoselective condensation step, the methoxyketone 7, an advanced intermediate in the synthesis of Sanfetrinem GV 104326.
Alkyl groups on the metal enhance the reactivity of the 'classical' zirconium enolate of 1-methoxycyclohexanone
Giacobbe, Simone A.,Rossi, Tino
, p. 3079 - 3082 (2007/10/03)
Compound 2 is the key intermediate in the preparation of our lead trinem antibiotic sanfetrinem 1a. In this communication it is described how a modified 'Evans' zirconium enolate of 1-methoxycyclohexanone is able to react with acetidinone 3 in the presence of LiHMDS under strict kinetic conditions, giving 2 with good yield and selectivity. Copyright (C) Elsevier Science Ltd.
