Concepedia

Wittig reactions with β-lactam carbonyls: a convenient means of protection. X-Ray crystal structure of p-nitrobenzyl-(2R,5R)-Z-7-methoxycarbonylmethylene-Z-3-(β-phthalimidoethylidene)-4-oxa-1-azabicyclo[3.2.0]heptane-2-carboxylate

Martin L. Gilpin, J. B. HARBRIDGE, T. Trefor Howarth, Trevor J. King

Journal of the Chemical Society Chemical Communications · 1981 · 13 citations · 0 references

Concepts

Natural SciencesChemistryMedicinal ChemistryOrganic ChemistryCrystal ChemistryOrganic SynthesisCrystal Structure AnalysisCrystal Structure TransformationsLactam MacrocyclesLactam SynthesisOzonolysisWittig Reactionβ-Lactam Antibiotics

Abstract

Clavulanic acid derivatives and penicillin Vesters undergo Wittig reactions at the β-lactam carbonyl and the β-lactam can be regenerated by low-temperature ozonolysis; the crystal structure of one of the products is reported.