Abstract

Serial radical 5-exo/6-exo cyclizations of a readily prepared hexopyranose derivative having unsaturations on-template at C-2 and off-template at C-7 lead to a tricyclic cage in which all but one of the stereocenters in an optically pure form of Woodward's densely functionalized carbocyclic precursor have been established, the «one» requiring an hydroxyl epimerization

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