Reaction of a functionalized β-vinylacyl anion equivalent with benzocyclobutenedione monoacetal, followed by methyl-lithium addition, yields a tricyclic structure having the requisite stereochemistry for elaboration to tetracyclines, as confirmed by a single crystal X-ray structure determination.
L. A. Spangler and J. S. Swenton, J. Chem. Soc., Chem. Commun., 1986, 828 DOI: 10.1039/C39860000828
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