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Paper | Special issue | Vol 67, No. 2, 2006, pp.621-628
Published online, 14th October, 2005
DOI: 10.3987/COM-05-S(T)29
Oxidative Cyclizations and the Synthesis of Lactones: A Streamlined Synthesis of epi-Crobarbatic Acid

John D. Brandt and Kevin D. Moeller*

*Department of Chemistry, Washington University, St. Louis, Missouri 63130, U.S.A.

Abstract

While anodic cyclizations have been shown to be compatible with the synthesis of lactones, the previous synthetic route to the starting materials was cumbersome and limited the overall utility of the approach. In this manuscript, a new strategy is reported that allows for very rapid synthesis of the electrolysis substrates. In addition, an efficient conversion of the ortho ester product obtained from the oxidative cyclization to a lactone acid is reported. The result is a dramatically improved synthetic strategy for the synthesis of functionalized tetrahydrofuranones.