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

TitleStereoselective synthesis of (-)-desethyleburnamonine, (-)-vindeburnol and (-)-3-epitacamonine: observation of a substrate dependent diastereoselectivity reversal of an aldol reaction
Publication TypeJournal Article
Year of Publication2016
AuthorsMondal, P, Argade, NP
JournalOrganic & Biomolecular Chemistry
Volume14
Issue44
Pagination10394-10406
Date PublishedOCT
AbstractStarting 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.
DOI10.1039/c6ob01438k
Type of Journal (Indian or Foreign)Foreign
Impact Factor (IF)3.559
Divison category: 
Organic Chemistry

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