Preparation and exploitation of versatile cyclohexanoid chiral building blocks

Efficient methodology for the preparation of two enantiopure cyclohexanoids having a bicyclo[2.2.1]octene background has been established starting from the same meso ene-1,4-diol by employing enzymatic and catalytic asymmetric desymmetrization procedures. On the basis of their inherent convex-face selectivity and thermal fragility, we utilize these chiral tricycles as synthetic equivalents of chiral p-benzoquinone and its hydro derivatives whose potential uses have been demonstrated by diastereo- and enantio-controlled synthesis of a wide variety of biologically active natural products.