New syntheses of (±)-tashiromine and (±)-epitashiromine via enaminone intermediates
The syntheses of the naturally occurring indolizidine alkaloid (±)-tashiromine and its unnatural epimer (±)-epitashiromine are demonstrated through the use of enaminone chemistry. The impact of various electron-withdrawing substituents at the C-8 position of the indolizidine core on the preparation...
| Main Authors: | , , |
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| Format: | Article |
| Language: | English |
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Beilstein-Institut
2016-12-01
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| Series: | Beilstein Journal of Organic Chemistry |
| Subjects: | |
| Online Access: | https://doi.org/10.3762/bjoc.12.256 |
| _version_ | 1818733378233434112 |
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| author | Darren L. Riley Joseph P. Michael Charles B. de Koning |
| author_facet | Darren L. Riley Joseph P. Michael Charles B. de Koning |
| author_sort | Darren L. Riley |
| collection | DOAJ |
| description | The syntheses of the naturally occurring indolizidine alkaloid (±)-tashiromine and its unnatural epimer (±)-epitashiromine are demonstrated through the use of enaminone chemistry. The impact of various electron-withdrawing substituents at the C-8 position of the indolizidine core on the preparation of the bicyclic system is described. |
| first_indexed | 2024-12-17T23:48:31Z |
| format | Article |
| id | doaj.art-f40a7eced75b436b8e26d77b52558bad |
| institution | Directory Open Access Journal |
| issn | 1860-5397 |
| language | English |
| last_indexed | 2024-12-17T23:48:31Z |
| publishDate | 2016-12-01 |
| publisher | Beilstein-Institut |
| record_format | Article |
| series | Beilstein Journal of Organic Chemistry |
| spelling | doaj.art-f40a7eced75b436b8e26d77b52558bad2022-12-21T21:28:15ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972016-12-011212609261310.3762/bjoc.12.2561860-5397-12-256New syntheses of (±)-tashiromine and (±)-epitashiromine via enaminone intermediatesDarren L. Riley0Joseph P. Michael1Charles B. de Koning2Department of Chemistry, University of Pretoria, Pretoria 0028, South AfricaMolecular Sciences Institute, School of Chemistry, University of the Witwatersrand, Wits 2050, Johannesburg, South AfricaMolecular Sciences Institute, School of Chemistry, University of the Witwatersrand, Wits 2050, Johannesburg, South AfricaThe syntheses of the naturally occurring indolizidine alkaloid (±)-tashiromine and its unnatural epimer (±)-epitashiromine are demonstrated through the use of enaminone chemistry. The impact of various electron-withdrawing substituents at the C-8 position of the indolizidine core on the preparation of the bicyclic system is described.https://doi.org/10.3762/bjoc.12.256alkaloidenaminoneepitashiromineindolizidinetashiromine |
| spellingShingle | Darren L. Riley Joseph P. Michael Charles B. de Koning New syntheses of (±)-tashiromine and (±)-epitashiromine via enaminone intermediates Beilstein Journal of Organic Chemistry alkaloid enaminone epitashiromine indolizidine tashiromine |
| title | New syntheses of (±)-tashiromine and (±)-epitashiromine via enaminone intermediates |
| title_full | New syntheses of (±)-tashiromine and (±)-epitashiromine via enaminone intermediates |
| title_fullStr | New syntheses of (±)-tashiromine and (±)-epitashiromine via enaminone intermediates |
| title_full_unstemmed | New syntheses of (±)-tashiromine and (±)-epitashiromine via enaminone intermediates |
| title_short | New syntheses of (±)-tashiromine and (±)-epitashiromine via enaminone intermediates |
| title_sort | new syntheses of tashiromine and epitashiromine via enaminone intermediates |
| topic | alkaloid enaminone epitashiromine indolizidine tashiromine |
| url | https://doi.org/10.3762/bjoc.12.256 |
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