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The IBX twist does it: Towards the synthesis of a recently isolated dihydropyranic azaphilone core framework, a 2-iodoxybenzoic acid (IBX)-mediated oxidative dearomatization was performed on a bicyclic substrate with excellent diastereoselectivity. Trifluoroacetic acid (TFA) esters were obtained as single diastereomers and water was shown to increase both the speed and diastereoselectivity of the reaction (see scheme).
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Boulangé et al. (2011) studied this question.
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