NATURAL-PRODUCTS CHEMISTRY - A SORT OF HETEROCYCLIC CHEMISTRY - REACTIONS OF SWEROSIDE WITH AMINES

Basic deglucosylation of secoiridoids has been investigated on swerosi de and its derivatives as model compounds. The deglucosylation was car ried out by propylamine and piperidine and in both cases the amine inc orporated into the secoiridoid derivative. With propylamine, sweroside 1 and 8,10-dihydrosweroside 2 gave the aza analogue 4 and 5 respectiv ely, however, from 2 a second bridged product 6 was formed, too, which could be obtained from the aglucone 3 as well. The incorporation of p iperidine took place at C-1 of 7 in the case of glucoside sweroside 1, but at C-3 of 9 in the case of aglucone 3 of 8,10-dihidrosweroside 2.