[1R,(+)]-6,6',12'-Trimethoxy-2,2'-dimethyloxyacanthan-7-ol

Description

A second bisbenzylisoquinoline base from Limacia cuspidata (Miers.) Hook. f. et Thorn., the alkaloid is separated from the accompanying !imacine by chromato? graphy on a silica column. It crystallizes in colourless prisms from MeOH-Me2 CO and has [α]_D + 110° (CHCI3). One hydroxyl group is present and the alkaloid yields the O-methyl ether as colourless needles, m.p. 210-2° C; [α]_D + 90°, (CHCI3), shown to be identical with N-methyl-dihydroepistephanine B. The structure has been established by chemical interconversions with limacine and cuspidaline (q.v.).

References

Tomita, Furukawa., Tetrahedron Lett., 4293 (I 966)
Structure:
Tomita, Furukawa, Fukagawa., l. Pharm. Soc., lapan, 87,793 (I967)