Alkaloid formation through N-oxide intermediates; regioselective synthesis of (±)-corytuberine by redox reaction
- 31 December 1979
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 2,p. 629-632
- https://doi.org/10.1039/p19800000629
Abstract
Reaction of (±)-reticuline N-oxide (1) with cuprous chloride in methanol followed by treatment with sodium hydrosulphite gave the aorphine alkaloid, (±)-corytuberine (8) in good yield. Protoberberine alkaloids, (±)coreximine (4) and (±)-scoulerine (5), were obtained by reaction of the N-oxide (1) with ferrous sulphate in methanol. On the other hand, formation of the phenol oxidative coupling product, (±)-orientalinone (9), from (±)-orientaline N-oxide (2) with cuprous chloride was less effective and formation of the protoberberine (7) from the N-oxide (2) with ferrous sulphate required acidic conditions.This publication has 10 references indexed in Scilit:
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