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

✍ Scribed by Jean-Christophe Galland; Sylvain Roland; Joël Malpart; Monique Savignac; Jean-Pierre Genet

Publisher: John Wiley and Sons
Year: 1999
Tongue: English
Weight: 302 KB
Volume: 1999
Category: Article
ISSN: 1434-193X
DOI: 10.1002/(sici)1099-0690(199903)1999:3<621::aid-ejoc621>3.0.co;2-a

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✦ Synopsis

An efficient diastereoselective multi-step synthesis of in the hydrogenation step to control the β-stereochemistry at the 1-position, and a π-allylpalladium ring-closure strategy is bicyclic 1β-methylcarbapenem antibiotic precursors has been developed, starting from the commercially available 4-used to form the functionalized carbapenem skeleton. acetoxyazetidin-2-one 4. Chiral ruthenium catalysts are used however, hydrogenation [6] of the exocyclic double bond [a

Results and Discussion

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