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

Letters in Organic Chemistry
2007.0

Abstract

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-alpha-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.

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