Alkaloid inspired spirocyclic oxindoles from 1,3-dipolar cycloaddition of pyridinium ylides
Cycloaddition reactions between pyridinium ylides and 3-alkenyl oxindoles that proceed in high yield and with very good regio- and diastereoselectivity are reported. The resulting cycloadducts have the same stereochemistry of biologically active oxindole alkaloids, such as strychnofoline.
| Main Authors: | Day, Jonathan, Uroos, Maliha, Castledine, Richard A., Lewis, William, McKeever-Abbas, Ben, Dowden, James |
|---|---|
| Format: | Article |
| Published: |
Royal Society of Chemistry
2013
|
| Online Access: | https://eprints.nottingham.ac.uk/2738/ |
Similar Items
Novel (3+2) dipolar cycloadditions of pyridinium ylides
by: Tongue, Tom
Published: (2017)
by: Tongue, Tom
Published: (2017)
Stereoselective synthesis of tetrahydroindolizines via catalytic formation of pyridinium ylides from diazo compounds
by: Day, Jonathan, et al.
Published: (2016)
by: Day, Jonathan, et al.
Published: (2016)
Towards the synthesis of anthecularin and spirocyclic oxindole alkaloids
by: Almutaleb, Arabya
Published: (2017)
by: Almutaleb, Arabya
Published: (2017)
Investigating the chemistry of pyridinium ylides
by: Abdullah, Rasha Azzam
Published: (2018)
by: Abdullah, Rasha Azzam
Published: (2018)
Electrochemical Deoxygenation of Benzylic Alcohols and Electrosynthesis of Spirocycles
by: Edmonds, Alex
Published: (2024)
by: Edmonds, Alex
Published: (2024)
The dipolar endofullerene HF@C60
by: Krachmalnikoff, Andrea, et al.
Published: (2016)
by: Krachmalnikoff, Andrea, et al.
Published: (2016)
Silyl Nitronate Cycloadditions Catalyzed by Cu(II)-Bisoxazoline
by: Dong, Li, et al.
Published: (2015)
by: Dong, Li, et al.
Published: (2015)
Densely functionalised spirocyclic oxetane-piperidine scaffolds for drug discovery
by: Geary, Gemma C., et al.
Published: (2017)
by: Geary, Gemma C., et al.
Published: (2017)
Parametric excitation of solitons in dipolar Bose Einstein condensates
by: Benseghir, A, et al.
Published: (2013)
by: Benseghir, A, et al.
Published: (2013)
On-Surface Azide-Alkyne Cycloaddition Reaction: Does It Click with Ruthenium Catalysts?
by: Li, Tiexin, et al.
Published: (2022)
by: Li, Tiexin, et al.
Published: (2022)
Novel spirocyclic tranylcypromine derivatives as lysine-specific demethylase 1 (LSD1) inhibitors
by: Shi, Y., et al.
Published: (2018)
by: Shi, Y., et al.
Published: (2018)
Synthesis of triazole-linked morpholino oligonucleotides via Cu1 catalysed cycloaddition
by: Palframan, Matthew J., et al.
Published: (2016)
by: Palframan, Matthew J., et al.
Published: (2016)
Solitons mobility in a dipolar Bose-Einstein condensate in an optical lattice
by: Umarov, Bakhram, et al.
Published: (2011)
by: Umarov, Bakhram, et al.
Published: (2011)
Selective Separation of Hydrogen Sulfide with Pyridinium-Based Ionic Liquids
by: Wang, X., et al.
Published: (2018)
by: Wang, X., et al.
Published: (2018)
Desulfurization of model oil using pyridinium-based ionic liquid
by: Nurul Umaira Nisa, Mazelan
Published: (2013)
by: Nurul Umaira Nisa, Mazelan
Published: (2013)
Desulfurization of model oil using pyridinium-based ionic liquid
by: Nurul Umaira Nisa, Mazelan
Published: (2013)
by: Nurul Umaira Nisa, Mazelan
Published: (2013)
Synthesis of spirocyclic enones by rhodium-catalyzed dearomatizing oxidative annulation of 2-alkenylphenols with alkynes and enynes
by: Kujawa, Szymon, et al.
Published: (2014)
by: Kujawa, Szymon, et al.
Published: (2014)
Vibration spectrum of a two-soliton molecule in dipolar Bose–Einstein condensates
by: Turmanov, B. Kh., et al.
Published: (2015)
by: Turmanov, B. Kh., et al.
Published: (2015)
Gemini pyridinium amphiphiles for the synthesis and stabilization of gold nanoparticles for drug delivery
by: Alea-Reyes, Maria E., et al.
Published: (2017)
by: Alea-Reyes, Maria E., et al.
Published: (2017)
Hydrazine carbodithioic acid pyridinium-2-yl methyl ester chloride.
by: Crouse, Karen Anne, et al.
Published: (2003)
by: Crouse, Karen Anne, et al.
Published: (2003)
Scattering of a two-soliton molecule by Gaussian potentials in dipolar Bose–Einstein condensates
by: Umarov, Bakhram A., et al.
Published: (2016)
by: Umarov, Bakhram A., et al.
Published: (2016)
Synthesis of novel 3,5-disubstituted-2-oxindole derivatives as antitumor agents against human nonsmall cell lung cancer
by: Nesi, G., et al.
Published: (2013)
by: Nesi, G., et al.
Published: (2013)
Design and synthesis of 2-oxindole based multi-targeted inhibitors of PDK1/Akt signaling pathway for the treatment of glioblastoma multiforme
by: Sestito, S., et al.
Published: (2015)
by: Sestito, S., et al.
Published: (2015)
Synthesis, structural and mass spectrometric investigations of pyridinium bis(thiosalicylato)mercurate(II)
by: Henderson, William, et al.
Published: (2019)
by: Henderson, William, et al.
Published: (2019)
Ionothermal synthesis of Zn-based metal organic frameworks in pyridinium ionic liquid
by: Ahmad, Haslina, et al.
Published: (2020)
by: Ahmad, Haslina, et al.
Published: (2020)
Functionalization of semiconductor surfaces by organic layers: Concerted cycloaddition versus stepwise free-radical reaction mechanism
by: Bilic, Ante, et al.
Published: (2006)
by: Bilic, Ante, et al.
Published: (2006)
Design, Synthesis and Molecular Docking Studies of Some Novel Spiro Derivatives By 1,3-Cycloaddition Reaction
by: Hasmaruddin, Nurul Syazana, et al.
Published: (2016)
by: Hasmaruddin, Nurul Syazana, et al.
Published: (2016)
Anti-continuum approach on nonlinear localized modes in dipolar Bose-Einstein condensates in optical lattice
by: Badarudin, M. H., et al.
Published: (2017)
by: Badarudin, M. H., et al.
Published: (2017)
Metal-free base-mediated oxidative annulation cascades to 3-substituted-3-hydroxyoxindole and its 3-spirocyclic derivative
by: Liu, Min, et al.
Published: (2017)
by: Liu, Min, et al.
Published: (2017)
Vinca alkaloids
by: Moudi, Maryam, et al.
Published: (2013)
by: Moudi, Maryam, et al.
Published: (2013)
Study of localized solutions of the nonlinear discrete model for dipolar BEC in an optical lattice by the homoclinic orbit method
by: Messikh, Azeddin, et al.
Published: (2013)
by: Messikh, Azeddin, et al.
Published: (2013)
Crystal structure 2-{[2-(3-phenylallylidene)hydrazin-1-yl]thiocarbonylsulfanylmethyl}pyridinium chloride
by: Low, May Lee, et al.
Published: (2014)
by: Low, May Lee, et al.
Published: (2014)
Measuring 19F shift anisotropies and 1H–19F dipolar interactions with ultrafast MAS NMR
by: Martini, Francesca, et al.
Published: (2015)
by: Martini, Francesca, et al.
Published: (2015)
Total synthesis of (−)-aritasone via the ultra-high pressure hetero-Diels–Alder dimerisation of (−)-pinocarvone
by: Uroos, Maliha, et al.
Published: (2017)
by: Uroos, Maliha, et al.
Published: (2017)
Semisynthesis of jerantinine alkaloids
by: Stanley, Paul
Published: (2017)
by: Stanley, Paul
Published: (2017)
Functionalized mesoporous silica nanoparticles templated by pyridinium ionic liquid for hydrophilic and hydrophobic drug release application
by: Zaharudin, Nurul Syahira, et al.
Published: (2020)
by: Zaharudin, Nurul Syahira, et al.
Published: (2020)
Facile access to a heterocyclic, sp3-rich chemical scaffold via a tandem condensation/intramolecular nitrone–alkene [3+2] cycloaddition strategy
by: Rawling, M.J., et al.
Published: (2015)
by: Rawling, M.J., et al.
Published: (2015)
Study of localized solutions of the nonlinear discrete model for dipolar Bose-Einstein condensate in an optical lattice by the homoclinic orbit method
by: Messikh, Azeddin, et al.
Published: (2012)
by: Messikh, Azeddin, et al.
Published: (2012)
Alkaloid Constituents of haplophyllum laeviusculum(Rutaceae)(Kandungan alkaloid daripada haplophyllum laeviusculum (Rutaceae)
by: Parimah Parhoodeh,, et al.
Published: (2012)
by: Parimah Parhoodeh,, et al.
Published: (2012)
Alkaloidal constituents of Tinospora crispa
by: Choudhary, M. Iqbal, et al.
Published: (2010)
by: Choudhary, M. Iqbal, et al.
Published: (2010)
Similar Items
-
Novel (3+2) dipolar cycloadditions of pyridinium ylides
by: Tongue, Tom
Published: (2017) -
Stereoselective synthesis of tetrahydroindolizines via catalytic formation of pyridinium ylides from diazo compounds
by: Day, Jonathan, et al.
Published: (2016) -
Towards the synthesis of anthecularin and spirocyclic oxindole alkaloids
by: Almutaleb, Arabya
Published: (2017) -
Investigating the chemistry of pyridinium ylides
by: Abdullah, Rasha Azzam
Published: (2018) -
Electrochemical Deoxygenation of Benzylic Alcohols and Electrosynthesis of Spirocycles
by: Edmonds, Alex
Published: (2024)