Diastereoselective Synthesis of Allosecurinine and Viroallosecurinine from Menisdaurilide
A new and versatile synthetic route to Securinega alkaloids is reported. The first synthesis of allosecurinine has been accomplished in seven steps and 40% yield, starting from (+)-menisdaurilide, using a vinylogous Mannich reaction as the key transformation. Similarly, viroallosecurinine has been s...
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| Veröffentlicht in: | Journal of organic chemistry 2008-10, Vol.73 (19), p.7657-7662 |
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| container_end_page | 7662 |
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| container_issue | 19 |
| container_start_page | 7657 |
| container_title | Journal of organic chemistry |
| container_volume | 73 |
| creator | Bardají, Gisela G Cantó, Mariona Alibés, Ramón Bayón, Pau Busqué, Félix de March, Pedro Figueredo, Marta Font, Josep |
| description | A new and versatile synthetic route to Securinega alkaloids is reported. The first synthesis of allosecurinine has been accomplished in seven steps and 40% yield, starting from (+)-menisdaurilide, using a vinylogous Mannich reaction as the key transformation. Similarly, viroallosecurinine has been synthesized from (−)-menisdaurilide. |
| doi_str_mv | 10.1021/jo801470u |
| format | Article |
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The first synthesis of allosecurinine has been accomplished in seven steps and 40% yield, starting from (+)-menisdaurilide, using a vinylogous Mannich reaction as the key transformation. 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| ispartof | Journal of organic chemistry, 2008-10, Vol.73 (19), p.7657-7662 |
| issn | 0022-3263 1520-6904 |
| language | eng |
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| source | MEDLINE; ACS Publications |
| subjects | Alkaloids - chemical synthesis Azepines - chemical synthesis Benzofurans - chemistry Chemistry Euphorbiaceae Exact sciences and technology Heterocyclic compounds Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives Heterocyclic Compounds, Bridged-Ring - chemical synthesis Lactones - chemical synthesis Organic chemistry Piperidines - chemical synthesis Preparations and properties Stereoisomerism |
| title | Diastereoselective Synthesis of Allosecurinine and Viroallosecurinine from Menisdaurilide |
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