An improved synthesis and resolution of (±)-cis,cis-2,2'-spirobiindane-1,1'-diol

Article abstract of DOI:10.1016/0957-4166(95)00201-Y

(±)-cis,cis-2,2'-spirobiindane-1,1'-diol (1) is synthesized stereoselectively in four steps beginning with 1-indanone in 68% overall yield. An improved resolution of diol 1 is described by preparing and separating diastereomeric mono-esters of 1 using (2S)-O-(tert-butyldimethylsilyl)mandeloyl chloride (10).