Oxidation Reaction of Bis-Quinolizidine System: Synthesis of New 2-Methyl-17-Oxosparteine and 2-Methyl-α-Isosparteine

Susceptibilities of two bis-quinolizidine systems: 2-methylsparteine and 2-phenylsparteine to oxidation reaction using K3Fe(CN)6, KMnO4 and Hg(CH3COO)2 have been determined. Of these two derivatives only 2-methylsparteine has been found to undergo oxidation giving new 2-methyl-17- oxosparteine and 2-methyl-α-isosparteine. The structures of the new compounds have been established by IR, MS and NMR spectroscopies. The experimental evidence has been supported by DFT calculations.