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The regiocontrolled rearrangement of 1,2-diols has been achieved by controlling the loading of BF 3 ·Et 2 O. Its applicability is showcased by the divergent synthesis of austrodoral, austrodoric acid, and 8- epi -11-nordriman-9-one, as well as a formal synthesis of siphonodictyal B and liphagal. A new light is shed on piancol-type rearrangements that will be useful in diversity-oriented synthesis of related natural products.
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Wang et al. (2017) studied this question.
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