Issue 44, 2016

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

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

Associated articles

Supplementary files

Article information

Article type
Paper
Submitted
05 Jul 2016
Accepted
03 Oct 2016
First published
03 Oct 2016

Org. Biomol. Chem., 2016,14, 10394-10406

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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