127127-61-1Relevant 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 via α,β-Unsaturated Acid Chlorides: Intermediates for Carbapenem Antibiotics
Manhas, M. S.,Ghosh, Malay,Bose, Ajay K.
, p. 575 - 580 (2007/10/02)
Stereocontrolled synthesis of α-vinyl β-lactams and their transformation to convenient intermediates for PS-5, PS-6, asparenomycin, and thienamycin are described.
The Reformatsky Type Reaction of Gilman and Speeter in the Preparation of Valuable β-Lactams in Carbapenem Synthesis: Scope and Synthetic Utility
Palomo, Claudio,Cossio, Fernando P.,Arrieta, Ana,Odriozola, Jose M.,Oiarbide, Mikel,Ontoria, Jesus M.
, p. 5736 - 5745 (2007/10/02)
The preparation of apppropriately substituted 3-alkyl β-lactams from the Reformatsky type reaction of Gilman and Speeter is described.Treatment of Schiff bases derived from α-methylcinnamaldehyde and amines with ethyl α-bromobutyrate or ethyl α-bromoisova
The α-Bromoester-Imine Condensation promoted by Zinc-Trimethylchlorosilane: A Stereospecific Short Formal Synthesis of (+/-)-Carbapenem Antibiotics and Realated Compounds
Cossio, Fernando P.,Odrizola, Jose M.,Oiarbide, Mikel,Palomo, Claudio
, p. 74 - 76 (2007/10/02)
Ethyl bromoacetate reacts with imines in the presence of zinc activated by trimethylchlorosilane to give high yields of 3-unsubstituted β-lactams.
6-substituted penem compounds
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, (2008/06/13)
The invention relates to 2-penem-3-carboxylic acid compounds of the formula STR1 in which Ra represents an organic radical bonded by a carbon atom to the ring carbon atom, a free, etherified or esterified hydroxy or mercapto group or a halogen atom, R1 represents hydrogen, an organic radical bonded by a carbon atom to the ring carbon atom, or an etherified mercapto group, and R2 represents a hydroxy group or an R2A radical that together with the carbonyl grouping --C(=O)-- forms a protected carboxyl group, and to salts of such compounds with salt-forming groups, processes for the manufacture of such compounds, pharmaceutical preparations containing compounds of the formula I with pharmacological properties, and their use. The compounds have antibiotic activity.
Useful Chemistry of 3-(1-Methylethylidene)-4-acetoxy-2-azetidinone: A Formal Synthesis of (+/-)-Asparenomycin C
Buynak, John D.,Rao, M. Narayana,Pajouhesh, Hassan,Chandrasekaran, Ramalakshmi Yegna,Finn, Kenneth,et al.
, p. 4245 - 4252 (2007/10/02)
3-(1-Methylethylidene)-4-acetoxy-2-azetidinone (5) was prepared from the addition of chlorosulfonyl isocyanate to 1-acetoxy-3-methylbuta-1,2-diene.Isolated as a stable crystalline solid, this material is a versatile intermediate and is used in a formal sy
A Short and Stereoselective Synthesis of the Carbapenem Antibiotic PS-5
Kametani, Tetsuji,Honda, Toshio,Nakayama, Atsushi,Sasakai, Yuko,Mochizuki, Tomoko,Fukumoto, Keiichiro
, p. 2228 - 2232 (2007/10/02)
The benzyl ester (3) and p-nitrobenzyl ester (PNB ester) (4) of the antibiotic PS-5 and the bis-protected PS-6 (5) were stereoselectively synthesised by application of the new carbon-carbon bond formation reaction at the C-4-position of 4-acetoxy-3-ethyl-
FACILE SYNTHESIS OF CARBAPENEM ANTIBIOTICS. THE FIRST AND SIMPLE STEREOSELECTIVE SYNTHESIS OF ANTIBIOTIC PS-5 BENZYL ESTER
Kametani, Tetsuji,Honda, Toshio,Nakayama, Atsushi,Fukumoto, Keiichiro
, p. 1967 - 1971 (2007/10/02)
Antbiotic PS-5 benzyl ester was stereoselectively synthesized by using a new carbon-carbon bond formation reaction at the C4-position of azeticin-2-one, as a key reaction.
