Strong Base Induced Cycloaddition of Homophthalic Anhydrides Leading to peri-Hydroxy Polycyclic Compounds

Article abstract of DOI:10.1021/jo00177a017

A new and exceptionally facile cycloaddition of the alkaline metal salt of homophthalic anhydrides (1a,b) is described.The anions of the anhydrides 1a,b undergo cycloadditions with various dienophiles (5-14) to give the corresponding peri-hydroxy polycyclic compounds (15-26) in good yields under extremely mild conditions, whereas thermal cycloaddition of 1a,b requires high temperatures.