Abstract
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 language | English |
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Pages (from-to) | 2702-2712 |
Number of pages | 11 |
Journal | Tetrahedron: Asymmetry |
Volume | 17 |
Issue number | 18 |
DOIs | |
Publication status | Published - 16 Oct 2006 |