Convenient new synthesis of snoutene [1] utilizing a dipolar cycloaddition of 4-phenyl-1,2,4-triazolin-3,5-dione
作者:Ihsan Erden、Armin de Meijere
DOI:10.1016/s0040-4039(00)92793-x
日期:1980.1
cycloadds to Nenitzescu's hydrocarbon 1 [6] with skeletal rearrangement. The major adduct 6 can conveniently be transformed to the azo compound 8, which upon photolysis or thermolysis yields up to 80 % pentacyclo[3.3.2.02,4,.03,7.o6,8]dec-9-ene (“ snoutene ”).
A new method for converting quinoneDiels–Alderadducts into cyclohexadiene derivatives is used for the synthesis of tricyclo[4,4,0,02,5]deca-3,7,9-triene, which rearranges to tricyclo[4,2,2,02,5]deca-3,7,9-triene at 70°.