Five-, Four-, and Three-Membered Carbocyclic Rings from 2-Deoxyribose by Intramolecular Nucleophilic Displacement Reaction

Article abstract of DOI:10.1021/jo00021a015

1,3-Dithianes such as 4, 9, 11, 13, and 19 derived from 2-deoxy-D-ribose (1) undergo intramolecular displacement reactions to give three-, four-, and five-membered carbocyclic rings (5, 10, 12, 15, and 20).Cyclopropanes are favored over the cyclobutanes when starting from the epoxides 9 or 11.Treatment of the tosylate 19 gives only a small yield of the corresponding cyclobutane 20, the major product being the ketone 21.