SYNTHESIS AND CHIROPTICAL PROPERTIES OF C3-PERHYDROTRIQUINACENE DERIVATIVES

Article abstract of DOI:10.1016/S0040-4020(01)81718-X

An efficient, enantioselective synthesis of C₃-triketone 1, starting from optically pure lactone 2, which is commercially available in both enantiomeric forms, is described.The absolute configuration of a chiral perhydrotriquinacene derivative is therefore established for the first time by chemical correlation.The stereochemical assignments are also confirmed by the circular dichroism of both (+)-1, which shows a positive Cotton effect, and the tribenzoate (+)-12, which presents a positive exciton chirality.