73521-59-2Relevant academic research and scientific papers
STUDIES RELATED TO THE STRUCTURES OF THE OLIVANIC ACIDS MM 13902, MM 4550 AND MM 17880. THREE β-LACTAM ANTIBIOTICS FROM STREPTOMYCES OLIVACEUS
Brown, Allan G.,Corbett, David F.,Eglington, A. John,Howarth, T. Trefor
, p. 2551 - 2562 (2007/10/02)
MM 13902, a β-lactam antibiotic isolated from Streptomyces olivaceus, has been identified as (5R,6R)-3--6--7-oxo-1-azabicyclohept-2-ene-2-carboxylic acid (2) by chemical and spectroscopic studies.The related olivanic acids MM 4550 and MM 17880 have been shown to be the corresponding 3-- and 3-(2-acetamidoethylthio)-derivatives (1 and 5), respectively.A number of carboxylate and sulphate esters of 1,2 and 5 have been prepared.A key reaction in the characterisation of 2 was the oxidative degradation of its C-2 monomethyl ester (12) in dimethylsulphoxide to methyl 3--5-pyrrole-2-carboxylate (22).The configuration of the C-6 substituent of 2 was determined by a stereospecific elimination reaction of its ethyl sulphate, p-nitrobenzyl carboxylate (19) to yield the 6-(E)-ethylidene derivative (32).MM 13902 was oxidised to MM 4550 with m-chloroperbenzoic acid.
Inversion of Configuration at C-8 in the Olivanic Acids: Conversion into the Thienamycins and Other Novel Derivatives
Corbett, David F.,Coulton, Steven,Southgate, Robert
, p. 3011 - 3016 (2007/10/02)
The inversion of stereochemistry at C-8 in the olivanic acids, MM 22383 (7) and MM 22381 (6), is described.The reaction of p-nitrobenzyl (5R,6S)-3--6--7-oxo-1-azabicyclohept-2-ene-2-carboxylate (8) with diethyl azodicarboxylate, triphenylphosphine, and formic acid afforded the 6- derivative (17), which upon alkaline hydrolysis gave the 6- derivative (18).Hydrolysis of the p-nitrobenzyl ester (18) furnished the sodium salt of N-acetyldehydrothienamycin (15), the (8R)-epimer of the olivanic acid MM 22383 (7).The 3-(2-acetamidoethylthio)-analogue, MM 22381 (6), was converted into N-acetylthienamycin (14) by performing a similar series of reactions on its p-nitrobenzyl ester (10).The transformation of the ester (18) to bis-protected thienamycin (22), via the C-3 thiol (21), is also described.Reaction of the olivanic acid esters (8) and (10) with diethyl azodicarboxylate, triphenylphosphine and hydrazoic acid resulted in the formation of the 6- derivatives (27) and (28).Subsequent hydrolysis provided (5R,6R)-3--6--7-oxo-1-azabicyclohept-2-ene-2-carboxylic acid (29) and the 3-(2-acetamidoethylthio)-analogue (30).
Carbapenum derivatives, a process for their preparation and their use in pharmaceutical compositions and intermediates
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, (2008/06/13)
The present invention provides antibiotic compounds of the formula: STR1 and salts and cleavable esters thereof wherein X is a SCH2 CH2 NH2 or YNH-COCH3 group where Y is a SCH2 CH2, trans -
