A new approach to the pancratistatin C-ring from D-Glucose: Ferrier rearrangement, pseudoinversion and Pd-catalyzed cyclizations

Article abstract of DOI:10.1016/S0040-4039(97)01325-7

A Ferrier rearrangement and β-hydroxyketone transposition are key steps in a route to a pancratistatin C-ring precursor. A key feature of the strategy is the pseudoinversion accomplished by β-hydroxyketone transposition, which allows convenient access from methyl α-D-glucopyranoside. Arylations of the C-ring by intramolecular reductive or non-reductive Pd-catalyzed conjugate addition have been demonstrated, utilizing the C1 hydroxyl to deliver the tethered aryl synthon.