Studies on the syntheses of heterocyclic compounds. Part 875. The total stereoselective retro mass spectral synthesis of (±)-emetine
- 1 January 1981
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- p. 920-925
- https://doi.org/10.1039/p19810000920
Abstract
Addition of 3,4-dihydro-6,7-dimethoxy-1-methylisoquinoline (5) to 3-methoxycarbonyl-1,6,7,11b-tetrahydro-9,10-dimethoxybenzo[a]quinolizin-4-one (4) produced 2-[3,4-dihydro-6,7-dimethoxy-1-isoquinolyl)methyl]-3-methoxycarbonyl-1,2,3,6,7,11b-hexahydro-9,10-dimethoxybenzo[a]quinolizin-4-one (6A). The same reaction of 3,4-dihydro-1-methyl-9H-pyrido[3,4-b]indole (15) with (4) afforded 2-(3,4-dihydro-9H-pyrido[3,4-b]-1-indolyl)methyl]-1,2,3,6,7,11b-hexahydro-9,10-dimethoxy-3-methoxycarbonylbenzo[a]quinolizin-4-one (16). The former Michael adduct (6A) was converted into (±)-emetine (1) in six steps.Keywords
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