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Valuable six-membered carbocycles including highly substituted benzenes, 1,4-cyclohexadienes, and 4-fluorocyclohexenes can be prepared from simple 1,5-enynes by iodonium-induced cyclization. This cyclization strategy was applied to the total synthesis of cybrodol, a sesquiterpenoid with a pentasubstituted aromatic core (see scheme).
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Crone et al. (2010) studied this question.
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