Synthesis of 1β??Methylcarbapenem Antibiotic Precursors by Cyclization Using π??Allylpalladium Complexes

…, S Roland, J Malpart, M Savignac…

Index: Galland, Jean-Christophe; Roland, Sylvain; Malpart, Joel; Savignac, Monique; Genet, Jean-Pierre European Journal of Organic Chemistry, 1999 ,  # 3  p. 621 - 626

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Citation Number: 14

Abstract

Abstract An efficient diastereoselective multi-step synthesis of bicyclic 1β- methylcarbapenem antibiotic precursors has been developed, starting from the commercially available 4-acetoxyazetidin-2-one 4. Chiral ruthenium catalysts are used in the hydrogenation step to control the β-stereochemistry at the 1-position, and a π- allylpalladium ring-closure strategy is used to form the functionalized carbapenem ...