SYNTHESIS AND ABSOLUTE-CONFIGURATION OF AXIALLY CHIRAL BINAPHTHOQUINONES

The synthesis of 2,3'-dimethyl-1,2'-binaphthalene-5,5',8,8'-tetrone (6 2) and 2,3'-dimethyl-1,2'-binaphthalene-1',4',5,8-tetrone (55), compou nds which are atropisomeric with the naturally occurring binaphthoquin ones (-)-isodiospyrin and (-)-8'-hydroxyisodiospyrin, respectively, is described. The binaphthyl linkages in these compounds were stereosele ctively constructed by using oxazoline chemistry. The stereochemical a ssignments were based on X-ray crystal structure determination and cir cular dichroic spectroscopy.