SYNTHESIS AND CHARACTERIZATION OF ALKALOID APORPHINE STEPHALAGINE AND ITS DERIVATIVES

Stephalagine was prepared by the reaction of chemical precursor via the formation of (2-(2-bromophenyl)-N-(2-(4-methoxybenzo[d][1,3]dioxol-5-yl)ethyl)acetamide,[M1]) and the formation of a heterocyclic compound (5-(2-bromobenzyl)-9-methoxy-7,8-dihydro-[1,3]dioxolo[4,5-g]isoquinoline, [M2]). Reduction of [M2] gave compound ((R)-5-(2-bromobenzyl)-9-methoxy-5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinoline, [M3]) which undergo amidation with (chloro propyl acetate) to give (propyl (R)-2-(5-(2-bromobenzyl)-9-methoxy-7,8-dihydro-[1,3]dioxolo[4,5-g]isoquinolin-6(5H)-yl)acetate, [M4]). Which in turn was converted to (propyl (R)-2-(4-methoxy-5,6,7a,8-tetrahydro-7H-[1,3]dioxolo[4',5':4,5]benzo[1,2,3-de]benzo[g]quinolin-7-yl)acetate, [M5]) via intramoleculer cyclization. The reaction of [M5] with (LiAlH4Me) gave the stephalegine [M6] in good yield. The intermediate compounds and the target molecules were identified by FT-IR spectra, 1HNMR.