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Tetrahedron Letters

Volume 48, Issue 12, 19 March 2007, Pages 2199-2203
Tetrahedron Letters

Spiroleucettadine: synthetic studies and investigations towards structural revision

https://doi.org/10.1016/j.tetlet.2007.01.088Get rights and content

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.

Graphical abstract

Density functional theory calculations were used to propose an alternative structure for spiroleucettadine.

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Acknowledgements

This work was supported by an Australian Postgraduate Award (N.A.). We thank Dr. Jonathan B. Baell for helpful discussions.

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