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 | |
| Publication status | Published - 31 Mar 2019 |
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Keywords
- Cannabis derivatives
- Cascade reactions
- Heterocycles
- Suzuki–Miyaura coupling
- Tetrahydrocannabinol
- Suzuki-Miyaura coupling
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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 journal › Article › Academic › peer-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
UR - http://www.scopus.com/inward/record.url?scp=85063584810&partnerID=8YFLogxK
U2 - 10.1002/ejoc.201900059
DO - 10.1002/ejoc.201900059
M3 - Article
C2 - 31423106
AN - SCOPUS:85063584810
VL - 2019
SP - 2289
EP - 2296
JO - European Journal of Organic Chemistry
JF - European Journal of Organic Chemistry
SN - 1434-193X
IS - 12
ER -