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Synfacts 2009(11): 1221-1221  
DOI: 10.1055/s-0029-1218094
Synthesis of Materials and Unnatural Products
© Georg Thieme Verlag Stuttgart ˙ New York

Long Helicenes by Alkyne Cycloisomerization

Contributor(s): Timothy M. Swager, David M. Chenoweth
P. Sehnal, I. G. Stará*, D. Šaman, M. Tichý, J. Míšek, J. Cvačka, L. Rulíšek, J. Chocholšouova, J. Vacek, G. Goryl, M. Szymonski*, I. Císařová, I. Star*
Academy of Sciences of the Czech Republic AND Charles University, Prague, Czech Republic and Jagiellonian University, Krakow, Poland
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Publication History

Publication Date:
22 October 2009 (online)

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Significance

Helicenes have many possible applications in the areas of materials science, asymmetric catalysis, and molecular recognition; ­however, long helicenes represent challenging synthetic targets. Reported here is a synthetic route to undecacyclic helicenes utilizing a cobalt-catalyzed intramolecular [2+2+2] alkyne cyclo­isomerization. This key step forms six new rings of the helicene backbone in a single transformation.