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Synfacts 2010(6): 0649-0649  
DOI: 10.1055/s-0029-1219982
Synthesis of Materials and Unnatural Products
© Georg Thieme Verlag Stuttgart ˙ New York

Radialene Synthesis

Contributor(s): Timothy M. Swager, D. Barney Walker
S. Shinozaki, T. Hamura, Y. Ibusuki, K. Fujii, H. Uekusa, K. Suzuki*
SORST, JST Agency, Tokyo, Tokyo Institute of Technology, Kwansei Gakuin University, Sanda and PRESTO, JST Agency, Tokyo, Japan
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Publication History

Publication Date:
20 May 2010 (online)

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Significance

The authors present a remarkable synthetic route to hexaradialene 1 that utilizes a thermally-driven ring-opening isomerization reaction to form the six exocyclic double bonds in the final step. The reaction proceeds efficiently provided that sufficiently bulky groups are tethered to the triannulated parent compound prior to isomerization, with both the syn and the anti precursors converted into 1.