Synthesis of the bioactive fungal natural product daldiquinone

Abstract

We report the first total synthesis of the biologically active fungal natural product daldiquinone (5), which was accomplished with a longest linear sequence of 8 steps in 41% overall yield. The construction of the unsymmetrical binaphthalene core was realized by a Suzuki-Miyaura cross-coupling in 88% yield on gram scale. Oxidation of naphthol 17 with IBX afforded the key naphthoquinone intermediate 18 in high yield (92%).