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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Bibliographic Details
Published in:Molecules (Basel, Switzerland) Switzerland), 2023-02, Vol.28 (4), p.1524
Main Authors: Guardia, Juan J, Fernández, Antonio, Justicia, José, Zentar, Houda, Alvarez-Manzaneda, Ramón, Alvarez-Manzaneda, Enrique, Chahboun, Rachid
Format: Article
Language:English
Subjects:
Aldehydes
bioactive natural products
Biosynthetic Pathways
Diterpenes
diterpenoids
Formic acid
Molecular Structure
Organic acids
Phenols
Skeleton
synthesis
taiwaniaquinoids
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Summary: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.
ISSN:1420-3049
1420-3049
DOI:10.3390/molecules28041524