103289-68-5Relevant articles and documents
β-Lactams from Ester Enolates and Silylimines: Enantioselective Synthesis of the trans-Carbapenem Antibiotics (+)-PS-5 and (+)-PS-6
Andreoli, Patrizia,Cainelli, Gianfranco,Panunzio, Mauro,Bandini, Elisa,Martelli, Giorgio,Spunta, Giuseppe
, p. 5984 - 5990 (2007/10/02)
A new synthetic route to the antibiotics (+)-PS-5 and (+)-PS-6 is described.The preparation involves a fully stereocontrolled reaction between the enantiomerically pure N-trimethylsilylimine of lactic or mandelic aldehyde and the lithium enolate of the tert-butyl butanoate or tert-butyl isovalerate, respectively.Conversion of the azetidinones obtained to 4-acetoxy derivatives via oxidative cleavage of the hydroxyethyl or hydroxybenzyl side chain and introduction of the necessary appendage in the position 4 of the azetidinone ring, followed by assemlage of the bicyclic ring system, afforded the natural trans-carbapenems (+)-PS-5 and (+)-PS-6.
β-Lactams from ester enolates and silylimines: Enantioselective synthesis of (+)-PS-5
Cainelli,Panunzio,Giacomini,Martelli,Spunta
, p. 6879 - 6880 (2007/10/02)
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