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

Basic deglucosylation of secoiridoids has been investigated on sweroside and its derivatives as model compounds. The deglucosylation was carried out by propylamine and piperidine and in both cases the amine incorporated into the secoiridoid derivative. With propylamine, sweroside 1 and 8,10-dihydrosweroside 2 gave the aza analogue 4 and 5 respectively, however, from 2 a second bridged product 6 was formed, too, which could be obtained from the aglucone 3 as well. The incorporation of piperidine 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.