SYNTHESIS OF 11-HYDROXY-2,3,9,10-TETRAMETHOXY-5,6,13,13A-TETRAHYDRO-8H-DIBENZOL[A,G]QUINOLIZINE . A CONTRIBUTION TO STRUCTURE OF STEPHAROTINE

(±)11-Hydroxy-2,3,9,10-tetramethoxy-5,6,13,13a-tetrahydro-8H-dibenzo[a,g]quinolizine (I) has been prepared by reduction of 11-hydroxy-2,3,9,10-tetramethoxybenzo[α]acridizinium bromide (13), afforded by hydrobromic acid catalyzed cyclization of quaternary salt 12 formed when 2,3-dimethoxy-4-hydroxybenzyl bromide (11) reacts with 6,7-dimethoxyisoquinoline-l-carboxaldoxime. Benzyl bromide 11 was prepared in four steps from the known 2,3-dimethoxy-4-hydroxybenzoic acid 7. The infrared spectrum of the title compound differs significantly from that of the alkaloid stepharotine. © 1969, American Chemical Society. All rights reserved.