82922-47-2Relevant academic research and scientific papers
β-Lactam antibiotics their preparation and their use
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, (2008/06/13)
The present invention provides a process for inversion of the absolute stereochemistry at the α-carbon atom of a C-6 substituent of a bicyclic carbapenem antibiotic via a phosphorus - azodicarboxylate mediated reaction. Novel azides, amines and formates a
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).
