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Synfacts 2011(3): 0275-0275  
DOI: 10.1055/s-0030-1259441
Synthesis of Materials and Unnatural Products
© Georg Thieme Verlag Stuttgart ˙ New York

The First Cycloiptycene

Contributor(s): Timothy M. Swager, Olesya Haze
K. Lou, A. M. Prior, B. Wiredu, J. Desper, D. H. Hua*
Kansas State University, Manhattan, USA
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Publication History

Publication Date:
16 February 2011 (online)

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Significance

The first cycloiptycene (5) was synthesized via a sequence of Diels-Alder reactions. An improved synthesis of the known heptiptycene tetraquinone 3 avoids byproduct formation during the first Diels-Alder reaction and gives an easily separated 1:1 mixture of isomeric adducts 2a and 2b in good yield. Double Diels-Alder reaction of 3 with one equivalent of heptiptycene 4 followed by oxidation affords the cyclododeciptycene quinone 5.