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Controlling Regiochemistry in the Gold-Catalyzed Synthesis of Unsaturated Spiroketals

Paulo H. S. Paioti, John M. Ketcham and Aaron Aponick*

*Department of Chemistry, Center for Heterocyclic Compounds, University of Florida, Gainesville, Florida 32611, United States, Email: aponickchem.ufl.edu

P. H. S. Paioti, J. M. Ketcham, A. Aponick, Org. Lett., 2014, 16, 5320-5323.

DOI: 10.1021/ol5024954 (free Supporting Information)


Abstract

A gold-catalyzed synthesis of unsaturated spiroketals is regulated by an acetonide protecting group which undergoes extrusion of acetone to deliver the desired spiroketals in good yields and diastereoselectivities. The reaction, which is carried out under very mild conditions employing AuCl as the catalyst, should be widely applicable.

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Key Words

acetals


ID: J54-Y2014