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Isolation and characterisation of a stable ozonide during an attempted synthesis of structural analogues of sarkomycin
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1983
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Structural AnaloguesCrystal StructureMedicinal ChemistryCombinatorial ChemistryHeterocyclicAttempted SynthesisBiochemistryNatural SciencesStable OzonideOrganic ChemistryAntibiotic SarkomycinChemistryHeterocycle ChemistryPharmacologyEnvelope Cs ConformationPharmaceutical ChemistrySynthetic ChemistryNatural Product Synthesis
We describe the conversion of 2,4-dimethyl-8-oxabicyclo [3.2.1] oct-6-en-3-one (1) into compounds resembling the antibiotic sarkomycin (3). An alternative synthetic pathway involving ozonolysis of (1) provided the crystalline ozonide (5), and the crystal structure of this compound showed that it existed in the envelope Cs conformation.