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A stereoselective approach for the formation of 2,8‐dioxabicyclo[3.3.1]nonane/nonene frameworks through the formation of 3‐C‐branched glycals encompassing the Claisen rearrangement of the carbohydrate‐derived allyl‐vinyl ethers and TMSOTf‐catalyzed acetalization reactions as key steps is revealed. A novel acetalization of 3‐C‐branched glycals with a tentative mechanism is proposed. The expedient protocol is evaluated by synthesizing a number of 2,8‐dioxabicyclo[3.3.1]nonane/nonene architectures.
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P. Sridhar (2013) studied this question.
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