Synthesis and Absolute Configuration of Axially Chiral Binaphthoquinones

Abstract

The synthesis of (+)-(S)-1',4-dihydroxy-2,3'-dimethyl-1,2'-binaphthalene-5,5',8,8'-tetrone (62) and (+)-(S)-4,5',8'-trihydroxy-2,3'-dimethyl-1,2'-binaphthalene-1',4',5,8-tetrone (55), compounds which are atrop-isomeric with the naturally occurring binaphthoquinones (–)-isodiospyrin and (–)-8'-hydroxyisodiospyrin, respectively, is described. The binaphthyl linkages in these compounds were stereoselectively constructed by using oxazoline chemistry. The stereochemical assignments were based on X-ray crystal structure determination and circular dichroic spectroscopy.