01217nas a2200145   4500008004100000245018800041210006900229260000800298300001600306490000700322520057400329100001900903700001900922856013000941       2016                        eng d00aStereoselective synthesis of (-)-desethyleburnamonine, (-)-vindeburnol and (-)-3-epitacamonine: observation of a substrate dependent diastereoselectivity reversal of an aldol reaction0 aStereoselective synthesis of desethyleburnamonine vindeburnol an  cOCT  a10394-104060 v143 aStarting 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.1 aMondal, Pravat1 aArgade, N., P.  uhttps://library.ncl.res.in/content/stereoselective-synthesis-desethyleburnamonine-vindeburnol-and-3-epitacamonine-observation