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

Organic & Biomolecular Chemistry Pub Date: 2016-10-03 DOI: 10.1039/C6OB01438K

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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