An asymmetric synthesis of (-)-deoxypodophyllotoxin

Article abstract of DOI:10.1021/jo00108a021

A Diels-Alder cycloaddition between the fumarate of methyl (S)-mandelate (22) and α-hydroxy-α-aryl-o-quinodimethane 21 produces an endo cycloadduct (23) in 58% yield. The preparation of the precursor to o-quinodimethane 21 and the conversion of cycloadduct 23 to optically pure (-)-deoxypodophyllotoxin (1) is described.