Org. and Biomol. Chem.
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Regioselective and stereoselective benzylidene installation and one-pot protection of D-mannose
DOI: 10.1039/C3OB40079D, PaperPratap S. Patil, Chia-Chen Lee, Yu-Wen Huang, Medel Manuel L. Zulueta, Shang-Cheng Hung
Regio- and stereoselective mono- and dibenzylidenations were developed and further incorporated into the one-pot synthesis of various thiomannoside building blocks.
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(+)-Fluorenylethylchloroformate (FLEC) - improved synthesis for application in chiral analysis and peptidomimetic synthesis
DOI: 10.1039/C3OB40218E, CommunicationMichelle A. Camerino, David K. Chalmers, Philip E. Thompson
The synthesis and application of a chiral Fmoc-equivalent (FLEC) has been achieved for combined resolution and protection of unusual amino acids for use in solid phase peptide synthesis.
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A novel convenient approach towards pyrrolo[1,2-b]pyridazines through a domino coupling-isomerization-condensation reaction
DOI: 10.1039/C3OB40157J, CommunicationMeng Wang, Cun Tan, Qian He, Yuyuan Xie, Chunhao Yang
A novel convenient approach towards pyrrolo[1,2-b]pyridazines through a Pd/Cu catalyzed domino reaction was developed. The products are versatile intermediates in many areas.
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Palladium(II)-catalyzed synthesis of functionalized indenones via oxidation and cyclization of 2-(2-arylethynylphenyl)acetonitriles
DOI: 10.1039/C3OB40103K, CommunicationXuxing Chen, Qian He, Yuyuan Xie, Chunhao Yang
A one-pot two-step synthesis of versatile indenones has been developed. The resulting 3-cyanoindenones can be converted to various valuable molecules.
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Total synthesis of (+)-pentamethylsalvianolic acid C
DOI: 10.1039/C3OB27478K, PaperBenjamin L. Alford, Helmut M. Hugel
The total synthesis of (+)-pentamethylsalvianolic acid C, a metabolite mimic from Salvia miltiorrhiza (Danshen).
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PEGylation enables the specific tumor accumulation of a peptide identified by phage display
DOI: 10.1039/C3OB27475F, PaperWalter Mier, Susanne Kramer, Sabine Zitzmann, Annette Altmann, Karin Leotta, Ursula Schierbaum, Martina Schnolzer, Michael Eisenhut, Uwe Haberkorn
PEGylation transforms "FROP-DOTA", a phage display derived peptide with weak in vivo properties, into a peptide with specific tumor uptake characteristics.
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From nonconjugation to conjugation: novel meso-OH substituted dipyrromethanes as fluorescence turn-on Zn2+ probes
DOI: 10.1039/C3OB40121A, PaperYubin Ding, Tong Li, Xin Li, Weihong Zhu, Yongshu Xie
meso-OH dipyrromethanes were developed as fluorescence turn-on Zn2+ probes based on Zn2+ promoted oxidation and subsequent coordination, showing no background fluorescence.
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Scaffold optimization in discontinuous epitope containing protein mimics of gp120 using smart libraries
DOI: 10.1039/C3OB27470E, PaperGwenn E. Mulder, H (Linda). C. Quarles van Ufford, Jeroen van Ameijde, Arwin J. Brouwer, John A. W. Kruijtzer, Rob M. J. Liskamp
A diversity of protein surface discontinuous epitope mimics is now rapidly and efficiently accessible.
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Domino synthesis of protochromic "ON-OFF-ON" luminescent 2-styryl quinolines
DOI: 10.1039/C3OB27270B, PaperRahime Cinar, Jan Nordmann, Elena Dirksen, Thomas J. J. Muller
Novel protochromic "ON-OFF-ON" luminescent 2-styryl quinolines have been synthesized by a coupling-isomerization-cyclization domino reaction.
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The first "ready-to-use" benzene-based heterotrifunctional cross-linker for multiple bioconjugation
DOI: 10.1039/C3OB40086G, PaperGuillaume Viault, Sebastien Dautrey, Nicolas Maindron, Julie Hardouin, Pierre-Yves Renard, Anthony Romieu
A benzene core was decorated with a set of three different and orthogonal reactive groups, to give the first aromatic heterotrifunctional cross-linker, enabling a rapid access to valuable luminescent (bio)conjugates.
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Phosphomolybdic and phosphotungstic acids as efficient catalysts for the synthesis of bridged 1,2,4,5-tetraoxanes from [small beta]-diketones and hydrogen peroxide
DOI: 10.1039/C3OB27239G, PaperAlexander O. Terent'ev, Ivan A. Yaremenko, Vera A. Vil', Igor K. Moiseev, Sergey A. Kon'kov, Valery M. Dembitsky, Dmitri O. Levitsky, Gennady I. Nikishin
Phosphomolybdic acid and phosphotungstic acid efficiently catalyze the addition of H2O2 to [small beta]-diketones.
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A novel three-component [5 + 1] heterocyclization leading to 2-azafluorenone synthesis and its polyfunctionalizations
DOI: 10.1039/C3OB40371H, CommunicationYing Li, Wei Fan, Hai-Wei Xu, Bo Jiang, Shu-Liang Wang, Shu-Jiang Tu
An efficient methodology for the synthesis of new and highly functionalized 2-azafluorenones via a three-component domino reaction involving C1-aryl acylation, C3-thiolation, and C4-cyanation has been developed.
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Phthalide: a direct building-block towards P,O and P,N hemilabile ligands. Application in the palladium-catalysed Suzuki-Miyaura cross-coupling of aryl chlorides
DOI: 10.1039/C3OB40198G, CommunicationJames McNulty, Kunal Keskar
Phthalide serves as an economical building block for the rapid assembly of useful P,O- and P,N-type hemilabile ligands.
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Reversible protein affinity-labelling using bromomaleimide-based reagents
DOI: 10.1039/C3OB40239H, CommunicationRamiz I. Nathani, Vijay Chudasama, Chris P. Ryan, Paul R. Moody, Rachel E. Morgan, Richard J. Fitzmaurice, Mark E. B. Smith, James R. Baker, Stephen Caddick
A mild and highly efficient, reversible protein biotinylation method using a hydrolytically stable linker and mild disassembly conditions is described.
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Towards the enantioselective synthesis of (-)-euonyminol - preparation of a fully functionalised lower-rim model
DOI: 10.1039/C3OB27187K, PaperMatthew J. Webber, Sarah A. Warren, Damian M. Grainger, Matthew Weston, Stacy Clark, Steven J. Woodhead, Lyn Powell, Stephen Stokes, Alexander Alanine, Jeffrey P. Stonehouse, Christopher S. Frampton, Andrew J. P. White, Alan C. Spivey
A stereoselective synthesis of [small beta]-dihydroagarofuran 4 is described. The route features a lactate Ireland-Claisen rearrangement to establish the quaternary stereocentre at C11 and a dealkylative intramolecular epoxide-opening by the C11 methyl ether to close the tetrahydrofuranyl C-ring.
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Enantioselective synthesis of 3,4-dihydropyran derivatives via a Michael addition reaction catalysed by chiral pybox-diph-Zn(II) complex
DOI: 10.1039/C3OB40246K, CommunicationSumit K. Ray, Subhrajit Rout, Vinod K. Singh
An enantioselective Michael addition of cyclic 1,3-dicarbonyls to 2-enoylpyridine N-oxides catalyzed by a chiral pybox-diph-Zn(II) complex has been developed. The corresponding Michael adducts have been obtained in high yields with up to >99% ee. The Michael adduct has been transformed to 2,4-disubstituted hexahydroquinoline.
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Multistep divergent synthesis of benzimidazole linked benzoxazole/benzothiazole via copper catalyzed domino annulation
DOI: 10.1039/C3OB27177C, PaperJen-Yu Liao, Manikandan Selvaraju, Chih-Hau Chen, Chung-Ming Sun
The amphiphilic reactivity of benzimidazole linked 2-chloroaniline has been exploited under Ullmann-like conditions for the construction of privileged bis-heterocycles.
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Steric, hydrogen-bonding and structural heterogeneity effects on the nucleophilic substitution of N-(p-fluorophenyldiphenylmethyl)-4-picolinium chloride in ionic liquids
DOI: 10.1039/C3OB40105G, PaperCameron C. Weber, Anthony F. Masters, Thomas Maschmeyer
The interplay between nucleophile and ionic liquid solvent effects on the kinetics of a nucleophilic substitution reaction are reported.
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An aerobic oxidation/homolytic substitution-cascade for stereoselective methylsulfanyl-cyclization of 4-pentenols
DOI: 10.1039/C3OB26590K, PaperPatrick Fries, Melanie Kim Muller, Jens Hartung
4-Pentenols (dihomoallylic alcohols) are oxidized by cobalt(II)-activated dioxygen in solutions of dimethyl disulfide and cyclohexa-1,4-diene to afford methylsulfanyl (CH3S)-functionalized tetrahydrofurans in up to 74% yield.
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Asymmetric synthesis of cyclo-archaeol and [small beta]-glucosyl cyclo-archaeol
DOI: 10.1039/C3OB27277J, PaperCatalina Ferrer, Peter Fodran, Santiago Barroso, Robert Gibson, Ellen C. Hopmans, Jaap Sinninghe Damste, Stefan Schouten, Adriaan J. Minnaard
An efficient asymmetric synthesis of cyclo-archaeol and [small beta]-glucosyl cyclo-archaeol is presented, and their occurrence in deep sea hydrothermal vents has been confirmed.
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