An alternative total synthesis of N-methylcaaverine through phenolic oxidation
- 1 January 1969
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society C: Organic
- No. 3,p. 502-505
- https://doi.org/10.1039/j39690000502
Abstract
Phenolic oxidation of 1,2,3,4-tetrahydro-7-hydroxy-1-(2-hydroxybenzyl)-6-methoxy-2-methylisoquinoline (Ib) afforded the dienone (IIb) in 2·4% yield, the dimeric benzylisoquinoline (XIa) in 1·1% yield, and an unknown carbonyl compound. Borohydride reduction of the dienone (IIb) gave the corresponding dienol(XVII), whose rearrangement in acidic media gave the 1-hydroxy-2-methoxyaporphine (XVIII). This aporphine was identical with (±)-N-methylcaaverine (XVIII), which was derived from the (±)-caaverine (XIX) by Eschweiler–Clarke reaction.Keywords
This publication has 0 references indexed in Scilit: