Abstract
A total synthesis of the highly strained natural product aquatolide has been achieved. The synthesis featured a photoinduced Wolff ring contraction reaction for the construction of bicyclo[2.1.1]hexane from diazo compound with a bicyclo[2.2.1]heptane skeleton. The eight-membered enone was built by a late-stage intramolecular Nozaki-Hiyama-Kishi vinylation reaction of steric bulky vinyl iodide and aldehyde.
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