Bulletin of the Chemical Society of Japan · 1982 · 15 citations · 9 references
Natural SciencesChemistryMedicinal ChemistryOrganic ChemistryStructure-activity RelationshipsSynthetic Medicinal ChemistryAmino Acid-derived Natural ProductsHeterocyclic ChemistryOrganic SynthesisRetrosynthetic AnalysisAmino Acid AmidesAmino Acid ChiralityAmino Acid DerivativesChiral Product SynthesisChiralityEnantioselective SynthesisStereochemistry Of Amino Acids
Abstract A short and high-yielding synthesis of optically active 3-aminonocardicinic acid (3-ANA) is described. The fourth component condensation reaction of N2-protected l-2,3-diaminopropanoic acid with p-benzyloxybenzaldehyde and butyl isocyanide gave directly the amide derivatives of 3-ANA, as a diastereomeric mixture, which was, after conversion of the amide group into the benzhydryl ester, led in good yield to a single disatereomer with natural chirality via epimerization. Deprotection of the 3-ANA derivative gave 3-ANA.
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Total synthesis of monocyclic β-lactam antibiotics, nocardicin A and D
Takashi Kamiya, Masashi Hashimoto, O. NAKAGUCHI et al. · Tetrahedron · 1979 · 51 citations