Spectral and Chemical Evidence for the Structure of C-Nor-D-Homoconessine

The rearranged product resulting from the action of lithium aluminium hydride upon holarrhenine tosylate (IV) in ether solution has been tentatively formulated by Uffer as C-nor-D-homoconessine (V). We found that holarrhenine mesylate (III) is converted into the same rearranged product on reacting with sodium borohydride in refluxing alcohol. The spectroscopic analysis of the rearranged product confirms the proposal of Uffer and gives results which completely parallel those obtained by Lukacs et al. in their study on the product of the reaction of the sulfonic esters of 12β-hydroxyconanine1 with aluminium dichlorohydride. Further converging data are afforded by a reaction sequence involving consecutive Hofmann degradations of the rearranged product (V).