Xu Chunping, Schwartz Chris, Raible Joseph, Dussault Patrick H
Department of Chemistry, University of Nebraska-Lincoln, Lincoln, Nebraska, 68588-0304.
Tetrahedron. 2009 Nov 21;65(47):9680-9685. doi: 10.1016/j.tet.2009.09.068.
The stereospecific intramolecular alkylation of a hydroperoxyacetal provides the basis for the first asymmetric synthesis of the dioxane propionate core of the peroxyplakorates. Chemoselective hydrometallation of an alkyne in the presence of a peroxide is used to introduce a synthon for the polyunsaturated side chains of the peroxyplakorates. The route suggests a general solution for the 1,2-dioxane unit in many peroxide natural products.