title: Synthesis of a Chiral Helical Molecular Template Based on trans-5,6,6a,7,8,12b-Hexahydro-1,12-dimethylbenzo[c]phenanthrene- 5,8-dione.
abstract: Reduction of trans-5,5,6a,7,8,12b-hexahydro-1,12-dimethylbenzo[c]phenanthrene-5,8-dione (1, R(1) = R(4) = H, R(2) = R(3) = CH(3)) with lithium aluminum hydride yielded stereoselectively (5RS,8RS)-trans-5,6,6a,7,8,12b-hexahydro-1,12-dimethylbenzo[c]phenanthrene-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 = COCH(3), and (5R,8R)-(-)-trans-5,6,6a,7,8,12b-hexahydro-1,12-dimethylbenzo[c]phenanthrene-5,8-diyl di-p-bromobenzoate (2a, X = p-BrC(6)H(4)CO), as well as the absolute configuration of the latter were obtained by X-ray crystallography.
authors.affiliation: Department of Organic Chemistry and Department of Inorganic Chemistry, The University of Sydney, New South Wales 2006, Australia.
authors.forename: Julie
authors.initials: J
authors.lastname: Cheung
authors.forename: Leslie D.
authors.initials: LD
authors.lastname: Field
authors.forename: Trevor W.
authors.initials: TW
authors.lastname: Hambley
authors.forename: Sever
authors.initials: S
authors.lastname: Sternhell