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

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

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 dramat...

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Bibliografiska uppgifter
Huvudupphovsmän: Van Ameijde, J, Horne, G, Wormald, M, Dwek, R, Nash, R, Jones, P, Evinson, E, Fleet, G
Materialtyp: Journal article
Språk:English
Publicerad: 2006
Beskrivning
Sammanfattning: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. © 2006 Elsevier Ltd. All rights reserved.

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