Carbapenem and penem antibiotics. I. Total synthesis and antibacterial activity of dl-asparenomycins A, B and C and related carbapenem antibiotics.

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Abstract
Racemic carbapenem antibiotics having a 1-(hydroxymethyl)ethylidene side-chain at C-6 [dl-asparenomycins A (54), B (37), C (53) and related compounds, 55, 56, 38, 59 and 45] were synthesized starting from the common intermediates 9a and 9b, and their antibacterial activities were examined. The synthesis involves transformation of a cyclic carbonate group into the 1-(hydroxymethyl)ethylidene moiety with a catalytic amount of 1,8-diazabicyclo[5,4,0]undec-7-ene (DBU) in an appropriate solvent, and deblocking of the p-methoxybenzyl ester group by the AICI3-anisole method.