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Spiroleucettadine: synthetic studies and investigations towards structural revision |
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| Authors: | Nicholas Aberle Simon PB Ovenden Keith G Watson Brian J Smith |
| Institution: | a The Walter and Eliza Hall Institute of Medical Research, 1G Royal Parade, Parkville 3050, Victoria, Australia b Department of Medical Biology, The University of Melbourne, Parkville 3010, Victoria, Australia c Defence Science and Technology Organisation, 506 Lorimer Street, Fishermans Bend 3207, Victoria, Australia |
| Abstract: | Synthetic efforts towards spiroleucettadine are described, including the enantioselective synthesis of the presumed biosynthetic precursor. High level density functional theory calculations were used to predict the 13C NMR shifts of possible alternative structures and, along with a re-evaluation of the available NMR data, allow the proposal of revised structures for this spirocyclic alkaloid. |
| Keywords: | Spiroleucettadine Density functional theory Oxidative cyclisations 13C NMR Predictions Biosynthesis |
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