β-Lactams from Ester Enolates and Silylimines: Enantioselective Synthesis of the trans-Carbapenem Antibiotics (+)-PS-5 and (+)-PS-6
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.
Andreoli, Patrizia,Cainelli, Gianfranco,Panunzio, Mauro,Bandini, Elisa,Martelli, Giorgio,Spunta, Giuseppe
p. 5984 - 5990
(2007/10/02)
Azetidinone derivatives and processes for production thereof
The invention relates to a method of producing an azetidinone derivative of the formula: STR1 which comprises reacting a compound of the formula STR2 with a compound of the formula STR3 and then subjecting the resulting compound to hydrolysis, the substituents above being as defined in the specification.
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(2008/06/13)
β-Lactams from ester enolates and silylimines: Enantioselective synthesis of (+)-PS-5
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Cainelli,Panunzio,Giacomini,Martelli,Spunta
p. 6879 - 6880
(2007/10/02)
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