SYNTHESIS OF A CHIRAL HELICAL MOLECULAR TEMPLATE BASED ON AHYDRO-1,12-DIMETHYLBENZO[C]PHENANTHRENE-5,8-DIONE

Reduction of ahydro-1,12-dimethylbenzo[c]phenanthrene-5,8-dione (1, R( 1)=R(4)=H, R(2)=R(3)=CH3) with lithium aluminum hydride yielded stereo selectively ,8,12b-hexahydro-1,12-dimethylbenzo[c]phenanthrene 2, X=H. These diols proved to be configurationally stable chiral molecular te mplates capable of straightforward modification by attachment of molec ular elements of different length and kind. The structures of the diac etate 2, X=COCH3, and trans-5,6,6a,7,8,12b-hexahydro-1,12-dimethylbenz o- [c]phenanthrene-5,8-diyl di-p-bromobenzoate (2a, X=p-BrC6H4CO), as well as the absolute configuration of the latter were obtained by X-ra y crystallography.