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Nucleophilic ring-opening of 1,6,10,14-tetraoxatetraspiro[2.1.25.1.29.1.213.13]hexadecane, a cyclooctane structure spiro-fused with four oxirane fragments, under the action of sodium azide was studied. Depending on the relative configuration of stereocenters in the starting compound, the reaction proceeded as an intramolecular transannular cyclization with the formation of a 9-oxabicyclo[3.3.1]nonane skeleton or as an independent nucleophilic opening of the oxirane rings, leading to tetraazido tetraols of the cyclooctane series. [ABSTRACT FROM AUTHOR]