Unprecedented Elimination Reactions of Cyclic Aldols: A New Biosynthetic Pathway toward the Taiwaniaquinoid Skeleton
The acid treatment of 6,7-seco-abietane dialdehydes gives, in high yield, the corresponding derivatives with the 4a-methyltetrahydrofluorene skeleton of taiwaniaquinoids. A mechanism involving the elimination of formic acid from the cyclic aldol intermediate is proposed here. This process can be pos...
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| Format: | Article |
| Language: | English |
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MDPI AG
2023-02-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/28/4/1524 |
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| author | Juan J. Guardia Antonio Fernández José Justicia Houda Zentar Ramón Alvarez-Manzaneda Enrique Alvarez-Manzaneda Rachid Chahboun |
| author_facet | Juan J. Guardia Antonio Fernández José Justicia Houda Zentar Ramón Alvarez-Manzaneda Enrique Alvarez-Manzaneda Rachid Chahboun |
| author_sort | Juan J. Guardia |
| collection | DOAJ |
| description | The acid treatment of 6,7-seco-abietane dialdehydes gives, in high yield, the corresponding derivatives with the 4a-methyltetrahydrofluorene skeleton of taiwaniaquinoids. A mechanism involving the elimination of formic acid from the cyclic aldol intermediate is proposed here. This process can be postulated as a new biogenetic pathway from abietane diterpenes to taiwaniaquinoids. Using this novel reaction, the first enantiospecific synthesis of bioactive natural cupresol and taxodal has been obtained. |
| first_indexed | 2024-03-11T08:22:24Z |
| format | Article |
| id | doaj.art-94d10ff90a954fa2a551af27cdf0539e |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-11T08:22:24Z |
| publishDate | 2023-02-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-94d10ff90a954fa2a551af27cdf0539e2023-11-16T22:19:40ZengMDPI AGMolecules1420-30492023-02-01284152410.3390/molecules28041524Unprecedented Elimination Reactions of Cyclic Aldols: A New Biosynthetic Pathway toward the Taiwaniaquinoid SkeletonJuan J. Guardia0Antonio Fernández1José Justicia2Houda Zentar3Ramón Alvarez-Manzaneda4Enrique Alvarez-Manzaneda5Rachid Chahboun6Departamento de Química Orgánica, Facultad de Ciencias, Instituto de Biotecnología, Universidad de Granada, 18071 Granada, SpainDepartamento de Química Orgánica, Facultad de Ciencias, Instituto de Biotecnología, Universidad de Granada, 18071 Granada, SpainDepartamento de Química Orgánica, Facultad de Ciencias, Instituto de Biotecnología, Universidad de Granada, 18071 Granada, SpainDepartamento de Química Orgánica, Facultad de Ciencias, Instituto de Biotecnología, Universidad de Granada, 18071 Granada, SpainÁrea de Química Orgánica, Departamento de Química y Física, Universidad de Almería, 04120 Almería, SpainDepartamento de Química Orgánica, Facultad de Ciencias, Instituto de Biotecnología, Universidad de Granada, 18071 Granada, SpainDepartamento de Química Orgánica, Facultad de Ciencias, Instituto de Biotecnología, Universidad de Granada, 18071 Granada, SpainThe acid treatment of 6,7-seco-abietane dialdehydes gives, in high yield, the corresponding derivatives with the 4a-methyltetrahydrofluorene skeleton of taiwaniaquinoids. A mechanism involving the elimination of formic acid from the cyclic aldol intermediate is proposed here. This process can be postulated as a new biogenetic pathway from abietane diterpenes to taiwaniaquinoids. Using this novel reaction, the first enantiospecific synthesis of bioactive natural cupresol and taxodal has been obtained.https://www.mdpi.com/1420-3049/28/4/1524bioactive natural productssynthesisditerpenoidstaiwaniaquinoids |
| spellingShingle | Juan J. Guardia Antonio Fernández José Justicia Houda Zentar Ramón Alvarez-Manzaneda Enrique Alvarez-Manzaneda Rachid Chahboun Unprecedented Elimination Reactions of Cyclic Aldols: A New Biosynthetic Pathway toward the Taiwaniaquinoid Skeleton Molecules bioactive natural products synthesis diterpenoids taiwaniaquinoids |
| title | Unprecedented Elimination Reactions of Cyclic Aldols: A New Biosynthetic Pathway toward the Taiwaniaquinoid Skeleton |
| title_full | Unprecedented Elimination Reactions of Cyclic Aldols: A New Biosynthetic Pathway toward the Taiwaniaquinoid Skeleton |
| title_fullStr | Unprecedented Elimination Reactions of Cyclic Aldols: A New Biosynthetic Pathway toward the Taiwaniaquinoid Skeleton |
| title_full_unstemmed | Unprecedented Elimination Reactions of Cyclic Aldols: A New Biosynthetic Pathway toward the Taiwaniaquinoid Skeleton |
| title_short | Unprecedented Elimination Reactions of Cyclic Aldols: A New Biosynthetic Pathway toward the Taiwaniaquinoid Skeleton |
| title_sort | unprecedented elimination reactions of cyclic aldols a new biosynthetic pathway toward the taiwaniaquinoid skeleton |
| topic | bioactive natural products synthesis diterpenoids taiwaniaquinoids |
| url | https://www.mdpi.com/1420-3049/28/4/1524 |
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