An Efficient Regioselective and Diastereoselective Synthesis of the Epoxy-quinol Functionality as Building Block for the Manumycin Antibiotics by the Sequence of Photooxygenation, Reduction and Weitz-Scheffer Epoxidation

Abstract

The photooxygenation of the acetanilide 2 affords the hydroperoxide 3, which by titanium-tetraisopropoxide-catalyzed reduction with dimethyl sulfide gives the corresponding quinol 4. Regioselective and diastereoselective Weitz-Scheffer epoxidation of the latter by tert-butyl hydroperoxide (TBHP) and DBU as base catalyst leads to the cis-epoxy quinol 1, the essential functionality in Manumycin antibiotics.