Abstract
Four-component-condensation of d-isoserine or l-isoserine, diphenylmethyl isocyanide and p-(benzyloxy)benzaldehyde was used to construct a functionalized β-lactam ring system which was transformed in 4 steps into 3-aminonocardicinic acid. A protected side chain of nocardicin D was synthesized from d-asparagine in 6 steps. Coupling of these units and further conversion to nocardicins A, B and D followed published procedures. Using l-asparagine for the synthesis of the side chain led to unnatural isonocardicin A. Biological activities of the products are compared.
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