Total synthesis of the epoxyquinol dimer (+)-panepophenanthrin: application of a diastereospecific biomimetic Diels–Alder dimerisation

Abstract

An asymmetric total synthesis of the novel and structurally complex epoxyquinol natural product (+)-panepophenanthrin has been accomplished, in which a biomimetic Diels–Alder dimerisation is a key step. The key monomeric precursor was assembled by an efficient Stille cross coupling of two readily available building blocks that upon standing underwent a diastereospecific dimerisation cascade in excellent yield.