Abstract
The preparation of a [2.2]indenoparacyclophane-based diene is described. Diels–Alder cycloadditions of this diene with N-methylmaleimide, N-phenylmaleimide and maleic anhydride occurred in good yields and anti-diastereoselectively only under high pressure conditions. Heterohelicenophanes were prepared by dehydrogenation of the Diels–Alder products with 10% Pd/C catalyst. A new helicenophanequinone was obtained by the reaction between the diene and 1,4-naphthoquinone.
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