Concise synthesis of the antidepressive drug candidate GSK1360707 by a highly enantioselective gold-catalyzed enyne cycloisomerization reaction.
@article{Teller2011ConciseSO, title={Concise synthesis of the antidepressive drug candidate GSK1360707 by a highly enantioselective gold-catalyzed enyne cycloisomerization reaction.}, author={Henrik Teller and Alois F{\"u}rstner}, journal={Chemistry}, year={2011}, volume={17 28}, pages={ 7764-7 } }
68 Citations
Gold‐Catalyzed Reactions Towards Diversity: From Simple Substrates to Functionalized Carbo‐ and Heterocycles
- ChemistryChemical record
- 2021
The main contributions in the field of gold catalysis from the group will be highlighted, emphasizing the recent reports, starting from 1,6‐ and 1,5‐enynes and then moving to keto‐ynes derivatives.
A Heteroleptic Dirhodium Catalyst for Asymmetric Cyclopropanation with α‐Stannyl α‐Diazoacetate. “Stereoretentive” Stille Coupling with Formation of Chiral Quarternary Carbon Centers
- ChemistryAngewandte Chemie
- 2020
The heteroleptic dirhodium paddlewheel catalyst 7 with a chiral carboxylate/acetamidate ligand sphere is uniquely effective in asymmetric cycloadditions with α‐diazo‐α‐trimethylstannyl (silyl, germyl) acetate, which shows for the first time that even chiral quarternary carbon centers can be made by the Stille–Migita reaction.
Gold-Catalyzed Synthesis of Small Rings
- ChemistryChemical reviews
- 2020
This review aims to provide a comprehensive summary of all the major advances and discoveries made in the gold-catalyzed synthesis ofcyclopropanes, cyclopropenes, cyclobutanes, Cyclobutenes, and their corresponding heterocyclic or heterosubstituted analogs.
Iridium-Catalyzed Cycloisomerization of N-Tethered 1,7-Enynes: Construction of Azabicyclo [5.1.0] octene System.
- Chemistry, BiologyThe Journal of organic chemistry
- 2020
An efficient method for the synthesis of azabicyclo [5.1.0] octenes through cycloismerization of nitrogen-tethered 1,7-enynes catalyzed by [IrCp*Cl2]2 was developed, which has potential applications in SAR studies of pharmaceutically interesting compounds and total synthesis of natural products.
Synergy of activating substrate and introducing C-H···O interaction to achieve Rh2(II)-catalyzed asymmetric cycloisomerization of 1,n-enynes
- Chemistry, BiologyScience China Chemistry
- 2020
We report the first Rh2(II)-catalyzed asymmetric cycloisomerization of activated enynes to provide cyclopropane-fused tetra-hydropyridines in good yields and excellent enantioselectivities under mild…
When Gold Meets Perfumes: Synthesis of Olfactive Compounds via Gold-Catalyzed Cycloisomerization Reactions.
- ChemistryOrganic letters
- 2020
An efficient, and mild synthetic route for the preparation of functionalized volatile oxa-bicyclo[4.1.0]-hept-4-ene (29 compounds, 44-98% isolated yields) has been developed relying on the…
A Comparative Study of Confining Ligands Derived from Methylated Cyclodextrins in Gold-Catalyzed Cycloisomerization of 1,6-Enynes
- ChemistryEuropean Journal of Organic Chemistry
- 2019
Asymmetric Synthesis of Azepine-Fused Cyclobutanes from Yne-Methylenecyclopropanes Involving Cyclopropanation/C-C Cleavage/Wagner-Meerwein Rearrangement and Reaction Mechanism.
- ChemistryThe Journal of organic chemistry
- 2019
Ring expansion of in situ generated cyclopropylmethyl cations via Wagner-Meerwein rearrangement to cyclobutanes is widely used in synthesis. However, the cyclopropylmethyl cations generated are…
Silver oxide mediated novel SET oxidative cyclization: stereoselective synthesis of 3-azabicyclo[n.1.0]alkanes.
- ChemistryChemical communications
- 2019
For the first time, silver oxide catalyzed SET-oxidative cyclization of an α-amidinoester tethered with an alkene, leading to a novel cyclopropane-fused cyclic amidine, allowing easy access to the pharmaceutically important 3-azabicyclo[n.1.0]alkane framework.
Gold Catalysis for Heterocyclic Chemistry: A Representative Case Study on Pyrone Natural Products.
- ChemistryAngewandte Chemie
- 2018
Alkynes are used as stable ketone surrogates, which can be activated under exceedingly mild conditions due to the pronounced carbophilicity of [LAu]+ fragments, and attack of a tethered ester carbonyl group onto the transient alkyne-gold complex then forges the pyrone ring in a fully regiocontrolled manner.
References
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In vivo microdialysis experiments in different animal models and receptor occupancy studies in rat confirmed that derivative 17 showed an appropriate profile to guarantee further progression of the compound.
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The triple reuptake inhibitor, GSK1360707, was synthesized via an efficient, scalable route, which features a vinyl triflate Suzuki coupling followed by a single-step, double alkylative…
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