Asymmetric Synthesis of 1,2-dioxanes: Approaches to the Peroxyplakoric Acids.
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.
Xu
Chunping
C
Department of Chemistry, University of Nebraska-Lincoln, Lincoln, Nebraska, 68588-0304.
Schwartz
Chris
C
Raible
Joseph
J
Dussault
Patrick H
PH