= Solution
Silver(I) promotes iodide departure, with precipitation of AgI. The <oxygen> of <dimethyl sulfoxide> substitutes at the iodine-bearing <carbon> to form an alkoxydimethylsulfonium intermediate. Triethylamine removes the <hydrogen> on that <carbon>; collapse forms C=O and breaks O–S, releasing dimethyl sulfide. The result is \b[<ketone> D by a <Kornblum oxidation>]. In arrow terms, the C–H <electrons> form the <carbonyl> <pi bond> as the O–S bond breaks. The <carbon> bearing iodine becomes the <carbonyl> <carbon>; the existing bridged <ether> and acetonide are spectators. The iodine centre loses its tetrahedral <stereochemistry> because it becomes trigonal planar.
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