Strained cis,cis,cis,trans-tribenzo[5.5.5.6]fenestranes are accessible in good yield by two-fold cyclodehydration of cis-2,6-diphenylspiro[cyclohexane-1,2′-indane]-1′,3′-diols and the particularly high acidity of their ‘inverted’ benzylic bridgehead C–H bonds, causing facile epimerization to the more stable all-cis-tribenzo[5.5.5.6]fenestranes, is shown.
B. Bredenkötter, D. Barth, D. Kuck and D. Kuck, Chem. Commun., 1999, 847 DOI: 10.1039/A902024A
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