STEREOCONTROLLED SYNTHESIS OF (.+-.)-DEOXYPODOPHYLLOTOXIN VIA THE BENZYL EQUIVALENT OF THE PETERSON REACTION

Thermal treatment of the o-hydroxymethylbenzylsilane (3) with an excess of maleic anhydride yielded the 1,2,3-trisubstituted tetrahydronaphthalene (8) with a cis configuration, via the benzyl equivalent of the Peterson reaction, which was converted stereoselectively into (±)-deoxypodophyllotoxin (13) in good overall yield via a regio- and stereo-selective sequence of reactions.