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Issue 44, 2016
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Stereoselective synthesis of (−)-desethyleburnamonine, (−)-vindeburnol and (−)-3-epitacamonine: observation of a substrate dependent diastereoselectivity reversal of an aldol reaction

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Abstract

Starting from (−)-acetoxyglutarimide, the enantioselective multistep synthesis of (−)-desethyleburnamonine, (−)-vindeburnol and (−)-3-epitacamonine has been demonstrated via a common hydroxyl-lactam intermediate with very good overall yields. The acetoxy function from (−)-acetoxyglutarimide was initially used as a handle to induce enantioselectivity and then as a latent source of the ketone carbonyl group. Most importantly, substrate dependent reversal of the diastereoselectivity in ester aldol reactions of hexahydroindolo[2,3-a]quinolizinones has been reported.

Graphical abstract: Stereoselective synthesis of (−)-desethyleburnamonine, (−)-vindeburnol and (−)-3-epitacamonine: observation of a substrate dependent diastereoselectivity reversal of an aldol reaction

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Publication details

The article was received on 05 Jul 2016, accepted on 03 Oct 2016 and first published on 03 Oct 2016


Article type: Paper
DOI: 10.1039/C6OB01438K
Citation: Org. Biomol. Chem., 2016,14, 10394-10406
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    Stereoselective synthesis of (−)-desethyleburnamonine, (−)-vindeburnol and (−)-3-epitacamonine: observation of a substrate dependent diastereoselectivity reversal of an aldol reaction

    P. Mondal and N. P. Argade, Org. Biomol. Chem., 2016, 14, 10394
    DOI: 10.1039/C6OB01438K

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