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Synthesis 2017; 49(08): 1849-1856
DOI: 10.1055/s-0036-1588386
DOI: 10.1055/s-0036-1588386
paper
Formal Synthesis of Bioactive Indole Alkaloids Eburnamonine, Eburnaminol, and Vindeburnol
Further Information
Publication History
Received: 19 October 2016
Accepted after revision: 04 December 2016
Publication Date:
13 January 2017 (online)
Abstract
Starting from (±)-3-acetoxyglutarimide, diastereoselective formal synthesis of indole alkaloids (±)-eburnamonine, (±)-eburnaminol, and (±)-vindeburnol have been demonstrated via a common intermediate (±)-1-hydroxy-12-tosyl-2,3,6,7,12,12b-hexahydroindolo[2,3-a]quinolizin-4(1H)-one in very good overall yields. The acetoxy group from (±)-3-acetoxyglutarimide was first used to induce the diastereoselectivity and also as a latent source of ketone carbonyl group. The stereoselective eliminations, reductions, and intramolecular cyclizations were the involved key steps.
Key words
hexahydroindoloquinolizinone - elimination - reduction - cyclizations - eburnamonine - eburnaminol - vindeburnolSupporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0036-1588386. NMR spectra of all the synthesized compounds are included.
- Supporting Information
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