Molecules (Feb 2023)

Unprecedented Elimination Reactions of Cyclic Aldols: A New Biosynthetic Pathway toward the Taiwaniaquinoid Skeleton

  • Juan J. Guardia,
  • Antonio Fernández,
  • José Justicia,
  • Houda Zentar,
  • Ramón Alvarez-Manzaneda,
  • Enrique Alvarez-Manzaneda,
  • Rachid Chahboun

DOI
https://doi.org/10.3390/molecules28041524
Journal volume & issue
Vol. 28, no. 4
p. 1524

Abstract

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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.

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