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 |
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Pages (from-to) | 2289-2296 |
Number of pages | 8 |
Journal | European Journal of Organic Chemistry |
Volume | 2019 |
Issue number | 12 |
DOIs | |
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