71766-69-3Relevant articles and documents
Reaction of Protoberberine-type Alkaloids. Part 13. Biogenetic Conversion of Protoberberine Alkaloids into Phthalideisoquinoline Alkaloids
Kondo, Yoshikazu,Imai, Jiro,Nozoe, Shigeo
, p. 919 - 926 (2007/10/02)
A new convenient and biogenetic-type conversion of the protoberberine alkaloids into the phthalideisoquinoline alkaloids is described.The phthalideisoquinoline 5,6-dimethoxy-3-(6,7-dimethoxyisoquinolin-1-yl)isobenzofuran-1(3H)-one (4) was derived from 8-norcoralyne chloride (1) via 13-oxidonorcoralyne (3) in a one-pot reaction consisting of dye-sensitized photo-oxygenation followed by treatment with sodium borohydride.The conversion of berberine chloride into (+/-)-β-hydrastine (21) was performed by a reaction sequence involving conversion of 8,13a-epidioxy-9,10-dimethoxy- 2,3-methylenedioxy-13-oxo-5,6,13,13a-tetrahydro-8H-dibenzoquinolizine (9) into 1-(2-carboxy-3,4-dimethoxybenzoyl)-3,4-dihydro-6,7-(methylenedioxy)isoquinoline (11) using pyridinium chloride, followed by methylation and reductive cyclization.