Issue 0, 1979
From the journal:

Journal of the Chemical Society, Perkin Transactions 1

Studies on the syntheses of heterocyclic compounds. Part 766. A total stereoselective synthesis of emetine and (±)-dihydroprotoemetine

Tetsuji Kametani,   Yukio Suzuki,   Hirofumi Terasawa  and  Masataka Ihara  

Abstract

Reaction of 3,4-dihydro-6,7-dimethoxy-1 -methylisoquinoline (3) with diethyl αγ-diethoxycarbonylglutaconate (2) in ethanol, followed by silica gel chromatography, formed 3-ethoxycarbonyl-6,7-dihydro-9.10-dimethoxybenzo[a]quinolizin-4-one (6). The same reaction of (3) with (2), followed by reduction with sodium borohydride, afforded 3-ethoxycarbonyl-2-diethoxycarbonylmethyl-1,2,3,6,7,11b-hexahydro-9,10-dimethoxybenzo[a]quinolizin-4-one(10).

Condensation of (3) with dimethyl 3-methoxyallylidenemalonate (11) gave 2,3,6,7-tetrahydro-9,10-dimethoxy-3-methoxycarbonyl-2-(ββ-dimethoxyethyl)benzo[a]quinolizin-4-one (13), which was converted to (±)-emetine (1) in seven steps and (±)-dihydroprotoemetine (2) in six steps.

Decarboxylation of the enamide form (22) furnished mainly the cis-substituted compound (23).

About
Cited by
Related
Download options Please wait...

Article information

DOI
https://doi.org/10.1039/P19790001211
Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1979, 1211-1217

Permissions

Request permissions

Studies on the syntheses of heterocyclic compounds. Part 766. A total stereoselective synthesis of emetine and (±)-dihydroprotoemetine

T. Kametani, Y. Suzuki, H. Terasawa and M. Ihara, J. Chem. Soc., Perkin Trans. 1, 1979, 1211 DOI: 10.1039/P19790001211

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Spotlight

Advertisements