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Review | Regular issue | Vol 91, No. 5, 2015, pp.931-958
Published online, 24th February, 2015
DOI: 10.3987/REV-15-818
■ Transition Metal-Catalyzed Intramolecular Cyclization of Propargyl Alcohols and Their Derivatives for the Synthesis of Highly Substituted Five-Membered Oxygen Heterocycles

Masahiro Egi* and Shuji Akai*

*Synthetic Medicinal Chemistry, Graduate School of Pharmaceutical Sciences, Osaka University, 1-6 Yamadaoka, Suita, Osaka 565-0871, Japan

Abstract

The transition metal-catalyzed intramolecular cyclization of propargyl alcohols and their derivatives has been widely utilized in the synthesis of five-membered oxygen heterocycles such as furans, hydrofurans, and furanones. Prerequisites for the efficient transformations into highly substituted target compounds include the regioselectivity of the cyclization step and the chemoselectivity of the transition metal-mediated activation of substrates. This review documents recent progress on the title reactions by categorizing the initial activation modes of substrates.