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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2 Citations (Scopus)
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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

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thermohaline circulation
Dronabinol
cross coupling
Derivatives
Scaffolds
Hydrides
hydrides
elimination

Keywords

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

Cite this

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title = "A revised modular approach to (–)-trans-Δ 8 -THC and derivatives through late-stage Suzuki–Miyaura cross-coupling reactions",
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.",
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author = "Bloemendal, {Victor R.L.J.} and Daan Sondag and Hidde Elferink and Boltje, {Thomas J.} and {van Hest}, {Jan C.M.} and Rutjes, {Floris P.J.T.}",
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A revised modular approach to (–)-trans-Δ 8 -THC and derivatives through late-stage Suzuki–Miyaura cross-coupling reactions. / Bloemendal, Victor R.L.J.; Sondag, Daan; Elferink, Hidde; Boltje, Thomas J.; van Hest, Jan C.M. (Corresponding author); Rutjes, Floris P.J.T. (Corresponding author).

In: European Journal of Organic Chemistry, Vol. 2019, No. 12, 31.03.2019, p. 2289-2296.

Research output: Contribution to journalArticleAcademicpeer-review

TY - JOUR

T1 - A revised modular approach to (–)-trans-Δ 8 -THC and derivatives through late-stage Suzuki–Miyaura cross-coupling reactions

AU - Bloemendal, Victor R.L.J.

AU - Sondag, Daan

AU - Elferink, Hidde

AU - Boltje, Thomas J.

AU - van Hest, Jan C.M.

AU - Rutjes, Floris P.J.T.

PY - 2019/3/31

Y1 - 2019/3/31

N2 - 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.

AB - 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.

KW - Cannabis derivatives

KW - Cascade reactions

KW - Heterocycles

KW - Suzuki–Miyaura coupling

KW - Tetrahydrocannabinol

KW - Suzuki-Miyaura coupling

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