Stereoselective synthesis of (-)-desethyleburnamonine, (-)-vindeburnol and (-)-3-epitacamonine: observation of a substrate dependent diastereoselectivity reversal of an aldol reaction
| Title | Stereoselective synthesis of (-)-desethyleburnamonine, (-)-vindeburnol and (-)-3-epitacamonine: observation of a substrate dependent diastereoselectivity reversal of an aldol reaction |
| Publication Type | Journal Article |
| Year of Publication | 2016 |
| Authors | Mondal, P, Argade, NP |
| Journal | Organic & Biomolecular Chemistry |
| Volume | 14 |
| Issue | 44 |
| Pagination | 10394-10406 |
| Date Published | OCT |
| 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. |
| DOI | 10.1039/c6ob01438k |
| Type of Journal (Indian or Foreign) | Foreign |
| Impact Factor (IF) | 3.559 |
Divison category:
Organic Chemistry
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