Novel quinone syntheses

Abstract

As indicated by the title, this dissertation deals with the investigation of the syntheses of a number of novel quinones. Chapter I deals with the syntheses of quinonoid derivatives of the compounds isobenzofuran and isoindole. These are the parent species of that series of heterocyclic compounds which contain a single heteroatom and are isoelectronic with naphthalene. They have been of considerable interest to workers in recent years, but have proved to be relatively unstable. We have therefore set out to prepare stable quinonoid derivatives of these. In Chapter II we have sought to develop, via regiospecific Diels-Alder additions, simple syntheses of some synthetically useful napthaquinonoid systems. The formation of many of these, required in the past as intermediates for the syntheses of a number of naturally occurring quinones, has previously proved tedious. Tae study of these addition reactions has afforded a direct route for the synthesis of the natural quinone, droserone. Finally, in Chapter III, some of the napthaquinones produced in Chapter II have been employed as intermediates in the syntheses of certain naturally occurring quinonoid species. These include a caryopterone and model compounds for the proposed syntheses of the anti biotics, Juglomycins A and B.