Title of article :
Positional isomerization of quinine and quinidine via rhodium on alumina catalysis: practical one-step synthesis of Δ3,10-isoquinine and Δ3,10-isoquinidine
Author/Authors :
Portlock، نويسنده , , David E. and Naskar، نويسنده , , Dinabandhu and West، نويسنده , , Laura and Seibel، نويسنده , , William Y.C. and Gu، نويسنده , , Titan and Krauss، نويسنده , , Howard J and Peng، نويسنده , , X.Sean and Dybas، نويسنده , , Paul M and Soyke، نويسنده , , Edward G and Ashton، نويسنده , , Stephen B and Burton، نويسنده , , Jonathan، نويسنده ,
Abstract :
The synthesis of Δ3,10-isoquinine (5Z,5E) and Δ3,10-isoquinidine (6Z,6E) was achieved in one-step through positional isomerization of the terminal alkene in the parent cinchona alkaloids using catalytic amounts of 5% Rh/Al2O3 and excess hydrochloric acid in refluxing 50% aqueous EtOH. The products were obtained in good yields as a mixture of E and Z geometric isomers and fully characterized using spectroscopic methods.
