Regiodivergent Synthesis of ortho- and para-Cannabinoquinones

Daiana Mattoteia, Orazio Taglialatela-Scafati, Eduardo Muñoz, Laureano de la Vega, Diego Caprioglio (Lead / Corresponding author), Giovanni Appendino (Lead / Corresponding author)

Research output: Contribution to journalArticlepeer-review

1 Citation (Scopus)

Abstract

Spurred by the remarkable biological profile of cannabinoquinoids, we have systematically investigated the periodinane oxidation of their resorcinolic precursors, discovering that the regiochemistry of oxidation, a critical maneuver for bioactivity, depends not only on the nature of the oxidant (λ3- vs. λ5-iodanes), but also on post-oxidative prototropic- and valence tautomeric equilibria that isomerize ortho-quinones to para-quinones. By complementary selection of the periodinane oxidant and by freezing prototropic equilibration with O-methylation, isomeric ortho- and para-quinones could be obtained from mono- and diphenolic cannabinoids, setting the stage for the exploration of novel areas of the biological space, and establishing a blueprint for the extension of this strategy to other classes of bioactive alkylresorcinols.

Original languageEnglish
Pages (from-to)7429-7434
Number of pages6
JournalEuropean Journal of Organic Chemistry
Volume2020
Issue number48
Early online date13 Oct 2020
DOIs
Publication statusPublished - 31 Dec 2020

Keywords

  • Iodanes
  • Oxidation
  • Phytocannabinoids
  • Quinones
  • Tautomerism

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