SYNTHESIS OF (+)-1,3,5,7-TETRAKIS3-TRISHOMOCUBANYLBUTA-1,3-DIYNYL>ADAMANTANE. THE FIRST OPTICALLY ACTIVE ORGANIC MOLECULE WITH T SYMMETRY AND OF KNOWN ABSOLUTE CONFIGURATION

Article abstract of DOI:10.1016/S0040-4020(01)87594-3

(-)-(1S,3S,5R,6S,8R,10R)-trishomocubanethanoic acid (5) of known absolute configuration and absolute rotation was converted into (+)-(1S,3S,5R,6S,8R,10R)-2-bromoethynyl-D₃-trishomocubane (27) of C₃ symmetry. 1,3,5,7-Tetraethynyladamantane (22), with Td symmetry, was prepared from 1,3,5,7-tetrakis(hydroxymethyl)adamantane (13).Coupling of the C₃-component 27 with the Td component 22 was successfully accomplished by Chodkiewicz and Cadiot's procedure providing (+)-1,3,5,7-tetrakis<2-(1S,3S,5R,6S,8R,10R)-D₃-trishomocubanylbuta-1,3-diynyl>adamantane (4) whose highest attainable static and time-averaged dynamic symmetry are T and (C₃)⁴ Λ T, respectively.