A revised modular approach to (–)-trans-Δ 8 -THC and derivatives through late-stage Suzuki–Miyaura cross-coupling reactions

Victor R.L.J. Bloemendal, Daan Sondag, Hidde Elferink, Thomas J. Boltje, Jan C.M. van Hest (Corresponding author), Floris P.J.T. Rutjes (Corresponding author)

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Abstract

A revised modular approach to various synthetic (–)-trans-Δ 8 -THC derivatives through late-stage Suzuki–Miyaura cross-coupling reactions is disclosed. Ten derivatives were synthesized allowing both sp 2 - and sp 3 -hybridized cross-coupling partners with minimal β-hydride elimination. Importantly, we demonstrate that a para-bromo-substituted THC scaffold for Suzuki–Miyaura cross-coupling reactions has been initially reported incorrectly in recent literature.

Original languageEnglish
Pages (from-to)2289-2296
Number of pages8
JournalEuropean Journal of Organic Chemistry
Volume2019
Issue number12
DOIs
Publication statusPublished - 31 Mar 2019

Keywords

  • Cannabis derivatives
  • Cascade reactions
  • Heterocycles
  • Suzuki–Miyaura coupling
  • Tetrahydrocannabinol
  • Suzuki-Miyaura coupling

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