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Review | Regular issue | Vol 89, No. 6, 2014, pp.1369-1391
Published online, 15th April, 2014
DOI: 10.3987/REV-14-795
Reductive Cyclization Reactions to Bicyclic Compounds Using Samarium Diiodide

Motoo Tori* and Masakazu Sono

*Department of Analytical Chemistry, Faculty of Pharmaceutical Sciences, Tokushima Bunri University, 180 Nishihamabouji, Yamashiro-machi, Tokushima, 770-8514, Japan

Abstract

This review covers reports on the one-electron reductive cyclization reactions affording bicyclic compounds, such as hydrindans, perhydronaphthalenes, perhydroguaianes, and other systems including five-, six-, seven-, and eight-membered carbocycles using SmI2. The substrate is aldehyde, ketone, or ester. The effect of additives, such as H2O, MeOH, HMPA, and NiI2, was studied. The mechanistic aspects recently investigated are also introduced.