Advances in the Synthesis of 3,7,9-Heteroanalogues of Bicyclo[3,3,1]nonane

The heteroanalogues of bicyclo[3,3,1]nonane are of great theoretical and practical interest, which has stimulated synthetic studies in this field. These compounds are used as physiologically active substances and as intermediate in organic synthesis (for example in the synthesis of heteroadamantanes); a heterobicyclononane fragment occurs in the structures of certain alkaloids. The compounds are convenient models for stereochemical and conformational studies.
Despite the very large number of novel studies on the synthesis of compounds of this type, relevant reviews are not available. The present review gives a systematic analysis of typical mechanisms of the synthesis and the synthetic scope of each method and the limits of its applicability are discussed.
The bibliography includes 140 references.