ol500835f_si_002.pdf (58.57 MB)
Synthesis and Reactivity of 1,2-Dioxolanes from β,γ-Epoxy Ketones
journal contribution
posted on 2014-05-16, 00:00 authored by Wynne
V. Kandur, Kathleen J. Richert, Curtis J. Rieder, Andrew M. Thomas, Chunhua Hu, Joseph W. Ziller, K. A. WoerpelFive-membered
ring peroxides were prepared in one step in 31–86%
yield from readily accessible β,γ-epoxy ketones and H2O2. The reaction proceeded via a tetrahydrofuran,
which was converted to the thermodynamically favored 1,2-dioxolane.
The product contains a leaving group, which can be displaced to synthesize
analogues of the plakinic acid natural products.