A CONVENIENT SYNTHESIS OF TRIQUINACENE-2-CARBOXYLIC ACID AND A NEW APPROACH TOWARDS THE SYNTHESIS OF DODECAHEDRANE

Article abstract of DOI:10.1016/0040-4020(81)80004-X

A practical synthesis of triquinacene-2-carboxylic acid 1 from the readily available Thiele's acid 2 is reported.Optically active 2-formamidotriquinacene 20 derived from (+)-1 was condensed with the acid chloride of (+)-1 to give the secondary amide 23 via 22.Compound 23 was then converted into the cyclic imidate salt 26 with the hope to eventually achieve the synthesis of the dodecahedrane nucleus (see 28).