Isolation synthesis and glycosidase inhibition profile of 3-epi-casuarine

Jeroen V. Ameijde, Graeme Horne, Mark R. Wormald, Raymond A. Dwek, Robert J. Nash, David Paul Wyn-Jones, Emma L. Evinson, George W. J. Fleet

Research output: Contribution to journalArticlepeer-review

38 Citations (Scopus)


3-epi-Casuarine, the first naturally occurring stereoisomer of casuarine, was isolated from Myrtus communis L. The glycosidase inhibition profile and NMR spectra of 3-epi-casuarine are compared with those of casuarine; the change in configuration at one of the six stereogenic centres causes a dramatic change in the conformation of the bicyclic system. The key step in the 6% overall yield synthesis of 3-epi-casuarine from d-gluconolactone is the efficient cyclization of a completely unprotected pentahydroxyaminomesylate to the pyrrolizidine nucleus. A low yield synthesis of casuarine is also reported.
Original languageEnglish
Pages (from-to)2702-2712
Number of pages11
JournalTetrahedron: Asymmetry
Issue number18
Publication statusPublished - 16 Oct 2006


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