Stereoselective Construction of 2,8-Dioxabicyclo[3.3.1]nonane/nonene Systems from 3-C-Branched Glycals†

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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