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Synthesis of 1β‐Methylcarbapenem Antibiotic Precursors by Cyclization Using π‐Allylpalladium Complexes
Author(s) -
Galland JeanChristophe,
Roland Sylvain,
Malpart Joël,
Savignac Monique,
Genet JeanPierre
Publication year - 1999
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/(sici)1099-0690(199903)1999:3<621::aid-ejoc621>3.0.co;2-a
Subject(s) - chemistry , bicyclic molecule , combinatorial chemistry , ring (chemistry) , catalysis , ruthenium , stereochemistry , antibiotics , organic chemistry , biochemistry
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 skeleton.