Synthesis of Substituted Cyclooctanols by a Samarium(II) Iodide Promoted 8-Endo Radical Cyclization Process

Article abstract of DOI:10.1021/jo00090a041

Samarium(II) iodide (SmI2) has been employed to promote an efficient 8-endo radical cyclization reaction of a variety of substituted olefinic ketones.Various substituted monocyclic, fused bicyclic, and bridged bicyclic cyclooctanols have been synthesized in fair to excellent yield via this protocol.In addition to delineating the synthetic potential of this reaction, experiments have been conducted to determine the source of reduced, noncyclized byproducts present in this and related SmI2-mediated reactions performed under protic conditions.