%A P Wipf
%A JK Jung
%J Journal of Organic Chemistry
%T Formal total synthesis of (+)-diepoxin ?
%X The highly oxygenated antifungal anticancer natural product (?)-diepoxin ? was prepared in 10 steps and in 15% overall yield from O-methylnaphthazarin. Highlights of the synthetic work include an Ullmann coupling and a possibly biomimetic oxidative spirocyclization for the introduction of the naphthalene ketal as well as the use of a retro-Diels-Alder reaction to unmask the reactive enone moiety in the naphthoquinone bisepoxide ring system. A novel highly bulky chiral binaphthol ligand was developed for a boron-mediated Diels-Alder reaction that constitutes a formal asymmetric total synthesis of (+)-diepoxin ?.
%N 20
%P 6319 - 6337
%V 65
%D 2000
%R 10.1021/jo000684t
%L pittir20548