Regioselective Cross-Coupling Reactions as an Entry into Biologically Relevant Bithiazoles: First Total Synthesis of Cystothiazole E

2001 ◽  
Vol 40 (17) ◽  
pp. 3184-3185 ◽  
Author(s):  
Thorsten Bach ◽  
Stefan Heuser
Keyword(s):  
Total Synthesis ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Biologically Relevant ◽  
Cross Coupling Reactions

A Revised Modular Approach to D8-THC and Derivatives Through Late-Stage Suzuki-Miyaura Cross-Coupling Reactions

2019 ◽  
Author(s):  
Victor Bloemendal ◽  
Floris P. J. T. Rutjes ◽  
Thomas J. Boltje ◽  
Daan Sondag ◽  
Hidde Elferink ◽  
...  
Keyword(s):  
Biological Activity ◽  
Late Stage ◽  
Medicinal Chemistry ◽  
Cross Coupling ◽  
Modular Approach ◽  
Coupling Reactions ◽  
One Pot ◽  
Biologically Relevant ◽  
Cross Coupling Reactions ◽  
Chemistry Research

<p>In this manuscript we describe a modular pathway to synthesize biologically relevant (–)-<i>trans</i>-Δ<sup>8</sup>-THC derivatives, which can be used to modulate the pharmacologically important CB<sub>1</sub> and CB<sub>2</sub> receptors. This pathway involves a one-pot Friedel-Crafts alkylation/cyclization protocol, followed by Suzuki-Miyaura cross-coupling reactions and gives rise to a series of new Δ<sup>8</sup>-THC derivatives. In addition, we demonstrate using extensive NMR evidence that similar halide-substituted Friedel-Crafts alkylation/cyclization products in previous articles were wrongly assigned as the para-isomers, which also has consequence for the assignment of the subsequent cross-coupled products and interpretation of their biological activity. </p> <p>Considering the importance of the availability of THC derivatives in medicinal chemistry research and the fact that previously synthesized compounds were wrongly assigned, we feel this research is describing a straightforward pathway into new cannabinoids.</p>

scholarly journals Natural Deep Eutectic Solvents as Sustainable Solvents for Suzuki­–Miyaura Cross-Coupling Reactions Applied to Imidazo-Fused Heterocycles

SynOpen ◽  
2018 ◽  
Vol 02 (04) ◽  
pp. 0306-0311 ◽  
Author(s):  
Pierre-Olivier Delaye ◽  
Mélanie Pénichon ◽  
Leslie Boudesocque-Delaye ◽  
Cécile Enguehard-Gueiffier ◽  
Alain Gueiffier
Keyword(s):  
Choline Chloride ◽  
Deep Eutectic Solvent ◽  
Cross Coupling ◽  
Deep Eutectic Solvents ◽  
Coupling Reactions ◽  
Biologically Relevant ◽  
Cross Coupling Reactions ◽  
Fused Heterocycles ◽  
Natural Deep Eutectic Solvents ◽  
Natural Deep Eutectic Solvent

Herein, we present the first Suzuki–Miyaura cross-coupling in a sustainable natural deep eutectic solvent (NaDES) applied to biologically relevant imidazo-fused scaffolds imidazo[1,2-a]pyridine and imidazo[1,2-b]pyridazine. The choline chloride/glycerol (1:2, mol/mol) NaDES allowed the functionalisation of diverse positions on the heterocycles with various boronic acids, by using 2.5 mol% of readily available Pd(OAc)2. Notably, the catalytic system proceeds without any ligands or additives, without protection from the atmosphere.

Palladium-Catalyzed Cross-Coupling Reactions in Total Synthesis

ChemInform ◽  
2005 ◽  
Vol 36 (42) ◽  
Author(s):  
K. C. Nicolaou ◽  
Paul G. Bulger ◽  
David Sarlah
Keyword(s):  
Total Synthesis ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Cross Coupling Reactions ◽  
Palladium Catalyzed

scholarly journals Total synthesis of tubastrine and 3-dehydroxy tubastrine by microwave-assisted cross-coupling reactions

Tetrahedron ◽  
2015 ◽  
Vol 71 (43) ◽  
pp. 8278-8284 ◽  
Author(s):  
Marianne Lorentzen ◽  
Annette Bayer ◽  
Magne O. Sydnes ◽  
Kåre B. Jørgensen
Keyword(s):  
Total Synthesis ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Microwave Assisted ◽  
Cross Coupling Reactions
Sign in / Sign up

Export Citation Format

Share Document