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Stereocontrolled and efficient access to all the diastereomers of 1,3,5,7-tetraol structural units was developed using a Prins cyclisation–reductive cleavage sequence applied to tetrahydropyran aldehydes. Furthermore, these tetraols can be selectively functionalized.

Graphical abstract: Diastereo- and enantioselective synthesis of 1,3,5,7-tetraol structural units using a Prins cyclisation–reductive cleavage sequence

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