Improved High-Yield Synthesis of Polycyclic Aromatic Hydrocarbon Amino Tribenzoates, Nucleophilic Components for Synthesis of Diol Epoxide-Nucleoside Adducts

This report describes an improved high-yield synthesis of amino tribenzoates derived through a trans-ring opening of diol epoxides. A significant difference in the relative reactivities of benzo[a]pyrene series-1 and series-2 diol epoxide diastereomers with LiN3 has been noted. Facile triacylation of the azido triols derived through this ring-opening with benzoyl cyanide and reduction using PtO2 afforded the corresponding amines in high yields.