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- Title
Unprecedented Elimination Reactions of Cyclic Aldols: A New Biosynthetic Pathway toward the Taiwaniaquinoid Skeleton.
- Authors
Guardia, Juan J.; Fernández, Antonio; Justicia, José; Zentar, Houda; Alvarez-Manzaneda, Ramón; Alvarez-Manzaneda, Enrique; Chahboun, Rachid
- Abstract
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.
- Subjects
ELIMINATION reactions; SKELETON; ABIETANE; DITERPENES; FORMIC acid; ALDOLS; NATURAL products
- Publication
Molecules, 2023, Vol 28, Issue 4, p1524
- ISSN
1420-3049
- Publication type
Article
- DOI
10.3390/molecules28041524