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Communication | Regular issue | Vol 32, No. 2, 1991, pp.205-207
Published online, 1st January, 1970
DOI: 10.3987/COM-90-5548
Bicyclic Ketals. A Tandem Oxymercuration-Solvomercuration Protocol

Richard R. Copp, Dan R. Bruss, Timothy R. Schwartz, and Bradford P. Mundy

*Department of Chemistry, Montana State University, Bozeman, Montana 59717, U.S.A.

Abstract

Oxymercuration of an enol ether takes palce faster than oxymercuration of an isolated alkene. When both functional groups are present in the same molecule, one can use a properly oriented hydroxyl group fixed from the oxymercuration process to participate in a solvomercuration of the second site. This tandem oxymercuration-solvomercuration protocol was applied to the synthesis of two natural products in the 6,8-dioxabicyclo[3.2.1]octane series.