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; Floris P.J.T. Rutjes

doi:10.1002/ejoc.201900059

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)

Bio-Organic Chemistry

Research output: Contribution to journal › Article › Academic › peer-review

9 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 language	English
Pages (from-to)	2289-2296
Number of pages	8
Journal	European Journal of Organic Chemistry
Volume	2019
Issue number	12
DOIs	https://doi.org/10.1002/ejoc.201900059
Publication status	Published - 31 Mar 2019

Funding

We kindly acknowledge funding by the H2020-FETOPEN-2016-2017 programme of the European Commission (Grant agreement number: 737266-ONE FLOW). We also gratefully acknowledge Abbas H. K. Al Temimi for assistance with HPLC purifications.

Keywords

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

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10.1002/ejoc.201900059

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Cite this

Bloemendal, V. R. L. J., Sondag, D., Elferink, H., Boltje, T. J., van Hest, J. C. M., & Rutjes, F. P. J. T. (2019). A revised modular approach to (–)-trans-Δ ⁸ -THC and derivatives through late-stage Suzuki–Miyaura cross-coupling reactions. European Journal of Organic Chemistry, 2019(12), 2289-2296. https://doi.org/10.1002/ejoc.201900059

Bloemendal, Victor R.L.J. ; Sondag, Daan ; Elferink, Hidde et al. / A revised modular approach to (–)-trans-Δ ⁸ -THC and derivatives through late-stage Suzuki–Miyaura cross-coupling reactions. In: European Journal of Organic Chemistry. 2019 ; Vol. 2019, No. 12. pp. 2289-2296.

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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. ",

keywords = "Cannabis derivatives, Cascade reactions, Heterocycles, Suzuki–Miyaura coupling, Tetrahydrocannabinol, Suzuki-Miyaura coupling",

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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Bloemendal, VRLJ, Sondag, D, Elferink, H, Boltje, TJ, van Hest, JCM & Rutjes, FPJT 2019, 'A revised modular approach to (–)-trans-Δ ⁸ -THC and derivatives through late-stage Suzuki–Miyaura cross-coupling reactions', European Journal of Organic Chemistry, vol. 2019, no. 12, pp. 2289-2296. https://doi.org/10.1002/ejoc.201900059

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

Research output: Contribution to journal › Article › Academic › peer-review

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KW - Cascade reactions

KW - Heterocycles

KW - Suzuki–Miyaura coupling

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Bloemendal VRLJ, Sondag D, Elferink H, Boltje TJ, van Hest JCM, Rutjes FPJT. A revised modular approach to (–)-trans-Δ ⁸ -THC and derivatives through late-stage Suzuki–Miyaura cross-coupling reactions. European Journal of Organic Chemistry. 2019 Mar 31;2019(12):2289-2296. doi: 10.1002/ejoc.201900059