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.
W. J. Cummins, M. G. B. Drew, J. Mann and E. B. Walsh, J. Chem. Soc., Perkin Trans. 1, 1983, 167 DOI: 10.1039/P19830000167
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