Sequenced reactions with samarium(II) iodide. Tandem intramolecular nucleophilic acyl substitution/intramolecular barbier cyclizations

Article abstract of DOI:10.1021/ja00118a007

Samarium(II) iodide has been employed to promote a tandem intramolecular nucleophilic acyl substitution/ intramolecular Barbier cyclization sequence, generating bicyclic and tricyclic ring systems in excellent yield and high diastereoselectivity. Additionally, a highly versatile ring expansion - cyclization sequence allows entry into several different naturally occurring tricyclic ring systems containing seven- and eight-membered rings.