185463-47-2Relevant academic research and scientific papers
Synthesis of a chiral helical molecular template based on trans-5,6,6a,7,8,12b-hexahydro-1,12-dimethylbenzo[c]phenanthrene-5,8-d ione
Cheung,Field,Hambley,Sternhell
, p. 62 - 66 (2007/10/03)
Reduction of trans-5,5,6a,7,8,12b-hexahydro-1,12-dimethylbenzo[c]phenanthrene-5,8-d ione (1, R1 = R4 = H, R2 = R3 = CH3) with lithium aluminum hydride yielded stereoselectively (5RS,8RS)-trans-5,6,6a,7,8,12b-hexahydro-1,12-dimethylbenzo[c]phenanth rene-5,8-diols 2, X = H. These diols proved to be configurationally stable chiral molecular templates capable of straightforward modification by attachment of molecular elements of different length and kind. The structures of the diacetate 2, X = COCH3, and (5R,8R)-(-)-trans-5,6,6a,7,8,12b-hexahydro-1,12-dimethylbenzo[c]phenan threne-5,8-diyl di-p-bromobenzoate (2a, X = p-BrC6H4CO), as well as the absolute configuration of the latter were obtained by X-ray crystallography.
