Chirality Transfer from the Oxidative Dearomatization of Axially Chiral Binols with Oxone under Mild Conditions.

Easily accessible axially chiral substituted binols (95 to >99% ee) undergo an oxidative dearomatization process with the system Oxone/NaHCO3/acetone, under mild conditions, to afford pentacyclic hemiacetalic cis-diols (94 to >99% ee), bearing two new stereogenic centers, through an efficient axial-to-central chirality transfer.

Selective Oxidative Dearomatization of Angular Tetracyclic Phenols by Controlled Irradiation under Air: Synthesis of an Angucyclinone-Type Double Peroxide with Anticancer Properties.

Angular tetracyclic p-peroxyquinols, p-quinols, and a pentacyclic double peroxide, showing anticancer properties, were synthesized from the corresponding phenols by an environmentally friendly solvent- and wavelength-controlled irradiation under air in the absence of an external photosensitizer.