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Synthesis of Cyclododeciptycene Quinones

2010; American Chemical Society; Volume: 132; Issue: 49 Linguagem: Inglês

10.1021/ja1088309

1943-2984

Kaiyan Lou, Allan M. Prior, Bernard Wiredu, J. Desper, Duy H. Hua,

Synthetic Organic Chemistry Methods

Cycloiptycenes are elusive and synthetically challenging molecules. We report the first synthesis of two substituted cyclododeciptycene tetraquinones via a sequence of intermolecular and intramolecular Diels-Alder reactions from cis,cis-heptiptycene tetraquinone 2 and substituted 7,16-dihydro-7,16-(o-benzeno)heptacenes 3. Heptiptycene tetraquinone 2 was made from triptycene bisquinone 4 and 1,4-dimethoxyanthracene in three steps, and 6,8,15,17-tetramethoxy-7,16-dihydro-7,16-(o-benzeno)heptacene (3a) was synthesized from triptycene bisquinone 4 and 1,4-dihydro-2,3-benzoxathiin-3-oxide in four steps. The structure of a cyclododeciptycene, 1a, was determined by a single-crystal X-ray analysis. The synthetic sequence is general and should allow the incorporation of various alkoxy and acetoxy substituents appended to the cycloiptycene framework.