Synthesis of an analogue of the naturally occuring Aristotelia indole alkaloid, fruticosoline

A synthesis of an analogue of the rare Aristotelia indole alkaloids is repo rted. The monoterpene, Pulegone, 1 on nitromethylation give nitromethylpule gone, 2, which on reduction with LiAlH4 and as well as with NaBH4 yield the compounds 3, 4 and 5. The amino-alcohol 5 is condensed with indolyloxalyl chloride 6 to furnish the alpha-ketoamide 7, which is converted to the corr esponding monoterpenoid indole alkaloid 8, an analogue of fruticosoline 9.