Article: Synthesis of Guaipyridine Alkaloids Rupestine M and L by Cycloaddition/Cycloreversion of an Intermediate 1,4-Oxazinone.
2023 Volume 55, Issue 15, Page(s) 2319–2324
Abstract: A new method to prepare 1,4-oxazinone intermediates was developed based on aza-conjugate addition of β-amino alcohols to electron-deficient alkyne precursors. A tandem intramolecular cycloaddition/cycloreversion reaction sequence was evaluated, leading ... ...
| Abstract | A new method to prepare 1,4-oxazinone intermediates was developed based on aza-conjugate addition of β-amino alcohols to electron-deficient alkyne precursors. A tandem intramolecular cycloaddition/cycloreversion reaction sequence was evaluated, leading to the synthesis of the guaipyridine alkaloid natural products rupestine M and L. Starting from (-)-citronellal and thus a known configuration of the C5 stereocenter, a revised absolute configuration of natural rupestine L is suggested based on optical rotation. |
|---|---|
| Language | English |
| Publishing date | 2023-02-02 |
| Publishing country | Germany |
| Document type | Journal Article |
| ZDB-ID | 2033062-5 |
| ISSN | 1437-210X ; 0039-7881 |
| ISSN (online) | 1437-210X |
| ISSN | 0039-7881 |
| DOI | 10.1055/s-0042-1751413 |
| Database | MEDical Literature Analysis and Retrieval System OnLINE |
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