T. Kametani, M. Takemura, M. Ihara*
1977
Citations
0
Influential Citations
3
Citations
Journal
Israel Journal of Chemistry
Abstract
Oxidation of 1,2,3,4-tetrahydro-7-hydroxy-6-methoxy-3-(4,5-dimethoxy-2-vinylphenyl)-2-methylisoquinoline (10), derived from the corresponding berbine methiodide (8), with lead tetraacetate, followed by acidic treatments, gave 5,6-dihydro-8-hydroxy-2,3,9-trimethoxy-5-methylbenzo[c]phenenthridine (20). By a similar procedure, 1,2,3,4-tetrahydro-7-hydroxy-6-methoxy-3-(4,5-methylenedioxy-2-vinylphenyl)-2-methylisoquinoline (11) was converted to cis-8-acetoxy-4b,5,6,10b-tetrahydro-9-methoxy-5-methyl-2,3-methylenedioxybenzo[c]phenanthridine (17), whose hydrolysis with hydrochloric acid followed by methylation with diazomethane furnished dihydronitidine (22).