Reaction of protoberberine-type alkaloids. Part 13. Biogenetic conversion of protoberberine alkaloids into phthalideisoquinoline alkaloids
- 1 January 1980
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 4,p. 919-926
- https://doi.org/10.1039/p19800000919
Abstract
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-dibenzo[a,g]quinolizine (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.This publication has 0 references indexed in Scilit: