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Keywords = taiwaniaquinoids

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16 pages, 6077 KB  
Article
Unprecedented Elimination Reactions of Cyclic Aldols: A New Biosynthetic Pathway toward the Taiwaniaquinoid Skeleton
by Juan J. Guardia, Antonio Fernández, José Justicia, Houda Zentar, Ramón Alvarez-Manzaneda, Enrique Alvarez-Manzaneda and Rachid Chahboun
Molecules 2023, 28(4), 1524; https://doi.org/10.3390/molecules28041524 - 4 Feb 2023
Cited by 1 | Viewed by 2271
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 [...] Read more.
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. Full article
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