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...
| Main Authors: | , , , , , , , |
|---|---|
| Format: | Journal article |
| Language: | English |
| Published: |
2006
|
| _version_ | 1797091590158680064 |
|---|---|
| author | Van Ameijde, J Horne, G Wormald, M Dwek, R Nash, R Jones, P Evinson, E Fleet, G |
| author_facet | Van Ameijde, J Horne, G Wormald, M Dwek, R Nash, R Jones, P Evinson, E Fleet, G |
| author_sort | Van Ameijde, J |
| collection | OXFORD |
| description | 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. |
| first_indexed | 2024-03-07T03:35:12Z |
| format | Journal article |
| id | oxford-uuid:bc0d2b4c-ec4f-4f2e-822e-5594286458cf |
| institution | University of Oxford |
| language | English |
| last_indexed | 2024-03-07T03:35:12Z |
| publishDate | 2006 |
| record_format | dspace |
| spelling | oxford-uuid:bc0d2b4c-ec4f-4f2e-822e-5594286458cf2022-03-27T05:21:30ZIsolation synthesis and glycosidase inhibition profile of 3-epi-casuarineJournal articlehttp://purl.org/coar/resource_type/c_dcae04bcuuid:bc0d2b4c-ec4f-4f2e-822e-5594286458cfEnglishSymplectic Elements at Oxford2006Van Ameijde, JHorne, GWormald, MDwek, RNash, RJones, PEvinson, EFleet, G3-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. |
| spellingShingle | Van Ameijde, J Horne, G Wormald, M Dwek, R Nash, R Jones, P Evinson, E Fleet, G Isolation synthesis and glycosidase inhibition profile of 3-epi-casuarine |
| title | Isolation synthesis and glycosidase inhibition profile of 3-epi-casuarine |
| title_full | Isolation synthesis and glycosidase inhibition profile of 3-epi-casuarine |
| title_fullStr | Isolation synthesis and glycosidase inhibition profile of 3-epi-casuarine |
| title_full_unstemmed | Isolation synthesis and glycosidase inhibition profile of 3-epi-casuarine |
| title_short | Isolation synthesis and glycosidase inhibition profile of 3-epi-casuarine |
| title_sort | isolation synthesis and glycosidase inhibition profile of 3 epi casuarine |
| work_keys_str_mv | AT vanameijdej isolationsynthesisandglycosidaseinhibitionprofileof3epicasuarine AT horneg isolationsynthesisandglycosidaseinhibitionprofileof3epicasuarine AT wormaldm isolationsynthesisandglycosidaseinhibitionprofileof3epicasuarine AT dwekr isolationsynthesisandglycosidaseinhibitionprofileof3epicasuarine AT nashr isolationsynthesisandglycosidaseinhibitionprofileof3epicasuarine AT jonesp isolationsynthesisandglycosidaseinhibitionprofileof3epicasuarine AT evinsone isolationsynthesisandglycosidaseinhibitionprofileof3epicasuarine AT fleetg isolationsynthesisandglycosidaseinhibitionprofileof3epicasuarine |