Online article for Non-subscribers

Pay per view

Heterocycles has a pay-per-view service for Non-subscribers.
You will be able to directly purchase the full text article through PayPal.
Your purchased Paper can be downloaded after the payment is completed.
An e-mail will be sent the URL to download the paper.
If you have any questions, please contact:

Price: ¥ 4,400 (Yen only)
Period: This Article can be accessed for 7 days.

Communication | Regular issue | Vol 12, No. 7, 1979, pp.893-896
Published online, 1st January, 1970
DOI: 10.3987/R-1979-07-0893
Biomimetic Synthesis of Protoberberine Alkaloids and Aporphine Alkaloids through N-Oxide Intermediates

Tetsuji Kametani* and Masataka Ihara

*Pharmaceutical Institute, Tohoku University, Aobayama, Sendai 980-8578, Japan


Reaction of (±)-reticuline N-oxide (3) with cuprous chloride in methanol, followed by treatment with sodium hydrosulphite, gave (±)-corytuberine (8) in excellent yield, while phenol oxidative coupling of (±)-orientaline N-oxide (4) was less effective under the same conditions. Treatment of 3 with ferrous sulphate in methanol afforded (±)-coreximine (5) and (±)-scoulerine (6), but formation of the protoberberine (7) from 4 with this reagent required acidic conditions.