Unprecedented Elimination Reactions of Cyclic Aldols: A New Biosynthetic Pathway toward the Taiwaniaquinoid Skeleton
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Guardia, Juan J.; Fernández, Antonio; Justicia, José; Zentar, Houda; Alvarez-Manzaneda Roldán, Ramón Jesús; [et al.]Fecha
2023-02-04Resumen
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.
Palabra/s clave
bioactive natural products
synthesis
diterpenoids
taiwaniaquinoids