Narasimhan, N. S. ; Mali, R. S. ; Kulkarni, B. K. (1983) Synthetic application of lithiation reactions-XVI : syntheses of (±) tetrahydropalmatine, (±) canadine, (±) stylopine and (±) sinactine Tetrahedron, 39 (12). pp. 1975-1982. ISSN 0040-4020
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Official URL: http://linkinghub.elsevier.com/retrieve/pii/S00404...
Related URL: http://dx.doi.org/10.1016/S0040-4020(01)91915-5
Abstract
N,N-Dimethyl-3,4-dimethoxy- and methylenedioxybenzylamines were lithiated and the organolithium intermediates treated with paraformaldehyde to give the 2-hydroxymethyl derivatives. The latter were converted to 7,8-dimethoxy- and methylenedioxyisochroman-3-ones through successive reaction with ClCOOEt, KCN and KOH. The isochromanones on condensation with homoveratrylamine or homopiperonylamine, followed by cyclisation and reduction furnished the protoberberine alkaloids.
| Item Type: | Article |
|---|---|
| Source: | Copyright of this article belongs to Elsevier Science. |
| ID Code: | 24150 |
| Deposited On: | 29 Nov 2010 10:20 |
| Last Modified: | 09 Jun 2011 10:02 |
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