Org. and Biomol. Chem.
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Synthesis, analysis and biological evaluation of novel indolquinone cryptolepine analogues as potential anti-tumour agents.
Org. Biomol. Chem., 2016, Accepted Manuscript
DOI: 10.1039/C5OB02408K, PaperAdam De Lecq Le Gresley, Venkat Gudivaka, Simon Carrington, Alex Sinclair, John E Brown
A small library of cryptolepine analogues were synthesised incorporating halogens and/or nitrogen containing side chains to optimise their interaction with the sugar-phosphate backbone of DNA to give improved binding and...
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DOI: 10.1039/C5OB02408K, PaperAdam De Lecq Le Gresley, Venkat Gudivaka, Simon Carrington, Alex Sinclair, John E Brown
A small library of cryptolepine analogues were synthesised incorporating halogens and/or nitrogen containing side chains to optimise their interaction with the sugar-phosphate backbone of DNA to give improved binding and...
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Categories: Royal Society of Chemistry
2,3-Di-O-picolinyl building blocks as glycosyl donors with switchable stereoselectivity
Org. Biomol. Chem., 2016, Accepted Manuscript
DOI: 10.1039/C6OB00107F, PaperJagodige P. Yasomanee, Archana R Parameswar, Papapida Pornsuriyasak, Nigam P Rath, Alexei V Demchenko
2-O-Picolinyl protected glycosyl donors lead to the formation of 1,2-trans glycosides with complete stereoselectivity. This is due to the participatory effect of the picolinyl nitrogen that is able to block...
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DOI: 10.1039/C6OB00107F, PaperJagodige P. Yasomanee, Archana R Parameswar, Papapida Pornsuriyasak, Nigam P Rath, Alexei V Demchenko
2-O-Picolinyl protected glycosyl donors lead to the formation of 1,2-trans glycosides with complete stereoselectivity. This is due to the participatory effect of the picolinyl nitrogen that is able to block...
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Synthetic studies towards putative yuremamine using an iterative C(sp3)-H arylation strategy
Org. Biomol. Chem., 2016, Accepted Manuscript
DOI: 10.1039/C6OB00110F, PaperJonathan Sperry, Matthew Calvert
An overview of an iterative, 8-aminoquinoline (AQ)-directed C(sp3)-H arylation strategy towards the pyrroloindole structure initially assigned to the alkaloid yuremamine is described. During initial efforts using a model indane system,...
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DOI: 10.1039/C6OB00110F, PaperJonathan Sperry, Matthew Calvert
An overview of an iterative, 8-aminoquinoline (AQ)-directed C(sp3)-H arylation strategy towards the pyrroloindole structure initially assigned to the alkaloid yuremamine is described. During initial efforts using a model indane system,...
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Recent developments in synthetic methods for benzo[b]heteroles
Org. Biomol. Chem., 2016, Accepted Manuscript
DOI: 10.1039/C6OB00219F, Review ArticleBin Wu, Naohiko Yoshikai
Benzo[b]heteroles containing heteroatoms other than nitrogen and oxygen have received considerable attention for their potential for applications in materials science. This poses an increasing demand for efficient, selective, and broad-scope...
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DOI: 10.1039/C6OB00219F, Review ArticleBin Wu, Naohiko Yoshikai
Benzo[b]heteroles containing heteroatoms other than nitrogen and oxygen have received considerable attention for their potential for applications in materials science. This poses an increasing demand for efficient, selective, and broad-scope...
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Synthesis of indoles and tryptophan derivatives via photoinduced nitrene C-H insertion
DOI: 10.1039/C5OB02563J, PaperLukas Junk, Uli Kazmaier
Functionalized indoles and tryptophans can be obtained from stannylated alkenes and o-iodoanilines via Stille coupling.
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Palladium-catalyzed Suzuki-Miyaura coupling of amides by carbon-nitrogen cleavage: general strategy for amide N-C bond activation
DOI: 10.1039/C6OB00084C, PaperGuangrong Meng, Michal Szostak
A unified strategy for the palladium-catalyzed Suzuki-Miyaura cross-coupling of amides with boronic acids for the synthesis of ketones by N-C bond activation is reported.
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FRET-based Cyanine Probes for Monitoring Ligation Reactions and their Applications to Mechanistic Studies and Catalyst Screening
Org. Biomol. Chem., 2016, Accepted Manuscript
DOI: 10.1039/C5OB02127H, PaperEhud Herbst, Doron Shabat
There is an ever-increasing need to find better methods to selectively connect two molecules under mild aqueous conditions on small scale. The process of finding such methods significantly relies upon...
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DOI: 10.1039/C5OB02127H, PaperEhud Herbst, Doron Shabat
There is an ever-increasing need to find better methods to selectively connect two molecules under mild aqueous conditions on small scale. The process of finding such methods significantly relies upon...
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Nitropyrrole natural products: Isolation, Biosynthesis and Total Synthesis
Org. Biomol. Chem., 2016, Accepted Manuscript
DOI: 10.1039/C5OB02599K, Review ArticleXiao-Bo Ding, Margaret A Brimble, Daniel Furkert
Nitropyrrole-containing natural products are relatively rare in nature. Known examples are limited to the [small beta]-nitropyrrole-containing pyrrolomycins and [small alpha]-nitropyrrole-containing nitropyrrolins and heronapyrroles. Their unique structures and interesting bioactivity are of ongoing...
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DOI: 10.1039/C5OB02599K, Review ArticleXiao-Bo Ding, Margaret A Brimble, Daniel Furkert
Nitropyrrole-containing natural products are relatively rare in nature. Known examples are limited to the [small beta]-nitropyrrole-containing pyrrolomycins and [small alpha]-nitropyrrole-containing nitropyrrolins and heronapyrroles. Their unique structures and interesting bioactivity are of ongoing...
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Copper(II)-Catalyzed C5 and C7 Halogenation of Quinolines Using Sodium Halides under Mild Conditions
Org. Biomol. Chem., 2016, Accepted Manuscript
DOI: 10.1039/C6OB00169F, CommunicationJun Xu, Xiaolei Zhu, Guobin Zhou, Beibei Ying, Pingping Ye, Lingying Su, Chao Shen, pengfei zhang
A simple and mild protocol for copper catalyzed halogenation of quinoline at C5 and C7 positions was developed, affording desired remote C-H activation products in moderate to good yields. This...
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DOI: 10.1039/C6OB00169F, CommunicationJun Xu, Xiaolei Zhu, Guobin Zhou, Beibei Ying, Pingping Ye, Lingying Su, Chao Shen, pengfei zhang
A simple and mild protocol for copper catalyzed halogenation of quinoline at C5 and C7 positions was developed, affording desired remote C-H activation products in moderate to good yields. This...
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Tandem Prins spirocyclization for the stereoselective synthesis of tetrahydrospiro[chroman-2,4'-pyran] derivatives
Org. Biomol. Chem., 2016, Accepted Manuscript
DOI: 10.1039/C5OB02639C, PaperVenkata Subba Reddy Basireddy, Hanuman Reddy V, Durgaprasad Medaboina, Sridhar Balasubramanian, YELLA VENKATA RAMI REDDY
A novel cascade strategy has been developed for the synthesis of tetrahydrospiro[chroman-2,4'-pyran] derivatives by condensation of aldehydes with 2-(5-hydroxy-3-methylenepentyl)phenol. The reaction proceeds smoothly in the presence of BF3.OEt2 under mild...
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DOI: 10.1039/C5OB02639C, PaperVenkata Subba Reddy Basireddy, Hanuman Reddy V, Durgaprasad Medaboina, Sridhar Balasubramanian, YELLA VENKATA RAMI REDDY
A novel cascade strategy has been developed for the synthesis of tetrahydrospiro[chroman-2,4'-pyran] derivatives by condensation of aldehydes with 2-(5-hydroxy-3-methylenepentyl)phenol. The reaction proceeds smoothly in the presence of BF3.OEt2 under mild...
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The Stereoselectivities of Tributyltin Hydride-Mediated Reductions of 5-Bromo-D-Glucuronides to L-Iduronides are Dependent on the Anomeric Substituent: Syntheses and DFT Calculations
Org. Biomol. Chem., 2016, Accepted Manuscript
DOI: 10.1039/C6OB00283H, PaperShifaza Mohamed, Elizabeth Krenske, Vito Ferro
One of the shortest synthetic routes to L-iduronic acid derivatives is via free radical reduction of the C-5 bromide of the corresponding protected D-glucuronic acid derivative. The epimerization of such...
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DOI: 10.1039/C6OB00283H, PaperShifaza Mohamed, Elizabeth Krenske, Vito Ferro
One of the shortest synthetic routes to L-iduronic acid derivatives is via free radical reduction of the C-5 bromide of the corresponding protected D-glucuronic acid derivative. The epimerization of such...
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An Efficient Synthesis of Iminoquinones by Chemoselective Domino ortho-Hydroxylation/oxidation/imidation Sequence of 2-Aminoaryl Ketones
Org. Biomol. Chem., 2016, Accepted Manuscript
DOI: 10.1039/C5OB02659H, PaperChandrasekar S., G Sekar
An efficient chemoselective domino oxidative homocoupling of 2-aminoaryl ketone in presence of 2-iodoxybenzoic acid (IBX) for the synthesis of iminoquinone has been developed. The domino reaction proceeds via three consecutive...
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DOI: 10.1039/C5OB02659H, PaperChandrasekar S., G Sekar
An efficient chemoselective domino oxidative homocoupling of 2-aminoaryl ketone in presence of 2-iodoxybenzoic acid (IBX) for the synthesis of iminoquinone has been developed. The domino reaction proceeds via three consecutive...
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One-pot multienzyme (OPME) systems for chemoenzymatic synthesis of carbohydrates
Org. Biomol. Chem., 2016, Accepted Manuscript
DOI: 10.1039/C6OB00058D, PerspectiveHai Yu, Xi Chen
Glycosyltransferase-catalyzed enzymatic and chemoenzymatic syntheses are powerful approaches for the production of oligosaccharides, polysaccharides, glycoconjugates, and their derivatives. Enzymes involved in the biosynthesis of sugar nucleotide donors can be combined...
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DOI: 10.1039/C6OB00058D, PerspectiveHai Yu, Xi Chen
Glycosyltransferase-catalyzed enzymatic and chemoenzymatic syntheses are powerful approaches for the production of oligosaccharides, polysaccharides, glycoconjugates, and their derivatives. Enzymes involved in the biosynthesis of sugar nucleotide donors can be combined...
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Rhodium-Catalyzed ortho C-H Bond Activation of Arylamines for the Synthesis of Quinoline Carboxylates
Org. Biomol. Chem., 2016, Accepted Manuscript
DOI: 10.1039/C6OB00170J, PaperSudalai Arumugam, Sunita Gadakh, Soumen Dey
The rhodium catalyzed annulation of anilines with alkynic esters providing for the high yield synthesis of quinoline carboxylates with excellent regioselectivity is described. This unprecedented reaction employs either formic acid...
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DOI: 10.1039/C6OB00170J, PaperSudalai Arumugam, Sunita Gadakh, Soumen Dey
The rhodium catalyzed annulation of anilines with alkynic esters providing for the high yield synthesis of quinoline carboxylates with excellent regioselectivity is described. This unprecedented reaction employs either formic acid...
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Construction of enantioenriched polysubstituted hexahydropyridazines via a sequential multicatalytic process merging palladium catalysis and aminocatalysis
Org. Biomol. Chem., 2016, Accepted Manuscript
DOI: 10.1039/C5OB02437D, CommunicationAnne-Sophie Marques, Maxime Giardinetti, Jerome Marrot, Vincent Coeffard, Xavier Moreau, Christine Greck
An efficient multicatalytic strategy for the construction of nitrogen-containing heterocycles has been reported. The powerful combination of organic and metal catalysis in a single vessel allowed the formation of enantioenriched...
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DOI: 10.1039/C5OB02437D, CommunicationAnne-Sophie Marques, Maxime Giardinetti, Jerome Marrot, Vincent Coeffard, Xavier Moreau, Christine Greck
An efficient multicatalytic strategy for the construction of nitrogen-containing heterocycles has been reported. The powerful combination of organic and metal catalysis in a single vessel allowed the formation of enantioenriched...
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3-Component synthesis of [small alpha]-substituted sulfonamides via Bronsted acid-catalyzed C(sp3)-H bond functionalization of 2-alkylazaarenes
DOI: 10.1039/C6OB00108D, CommunicationT. Beisel, J. Kirchner, T. Kaehler, J. Knauer, Y. Soltani, G. Manolikakes
A Bronsted acid-catalyzed addition of 2-alkylazaarenes to in situ generated N-sulfonylimines through selective C(sp3)-H bond functionalization has been developed.
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Regioselective Ir(III)- catalyzed C-H alkynylation directed by 7-azaindoles
Org. Biomol. Chem., 2016, Accepted Manuscript
DOI: 10.1039/C6OB00179C, PaperBin Liu, Xin Wang, Zemei Ge, Runtao Li
Herein we reported a novel iridium(III)-catalyzed ortho-mono-alkynylation of 7-azaindoles under mid conditions. This approach provides a general and straight forward access to form novel 7-azaindole derivatives with ample substrate scope...
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DOI: 10.1039/C6OB00179C, PaperBin Liu, Xin Wang, Zemei Ge, Runtao Li
Herein we reported a novel iridium(III)-catalyzed ortho-mono-alkynylation of 7-azaindoles under mid conditions. This approach provides a general and straight forward access to form novel 7-azaindole derivatives with ample substrate scope...
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Reversible Morphological Changes of Assembled Supramolecular Amphiphiles Triggered by pH-Modulated Host-Guest Interactions
Org. Biomol. Chem., 2016, Accepted Manuscript
DOI: 10.1039/C6OB00109B, PaperMark Anthony Olson, Marco S Messina, Jonathan R Thompson, Trenton J Dawson, Amanda N Goldner, Daryl K Gaspar, Mariela Vazquez, Jessica A Lehrman, Andrew C.-H. Sue
Reversible template-directed micellar-size and shape modulation by virtue of host-guest reversible docking of molecular templates at the micellar-solvent interface was achieved in water. By combining a [small pi]-electron deficient bipyridinium-based gemini...
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DOI: 10.1039/C6OB00109B, PaperMark Anthony Olson, Marco S Messina, Jonathan R Thompson, Trenton J Dawson, Amanda N Goldner, Daryl K Gaspar, Mariela Vazquez, Jessica A Lehrman, Andrew C.-H. Sue
Reversible template-directed micellar-size and shape modulation by virtue of host-guest reversible docking of molecular templates at the micellar-solvent interface was achieved in water. By combining a [small pi]-electron deficient bipyridinium-based gemini...
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Approach to 2-(arylthio)imidazoles and imidazo[2,1-b]thiazoles from imidazo[2,1-b][1,3,4]thiadiazoles by ring-opening and -reconstruction
Org. Biomol. Chem., 2016, Accepted Manuscript
DOI: 10.1039/C6OB00102E, PaperBenyi Shi, Zhouhe Zhu, Yi-Shuo Zhu, Dagang Zhou, jinyuan wang, Panpan Zhou, huanwang jing
Highly efficient one-pot synthesis of imidazo[2,1-b]thiazole derivatives has been developed by a ring-opening and ring-closing reconstruction of imidazo[2,1-b][1,3,4]thiadiazoles with phenylacetylene in the presence of potassium tert-butoxide (t-BuOK) under very mild...
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DOI: 10.1039/C6OB00102E, PaperBenyi Shi, Zhouhe Zhu, Yi-Shuo Zhu, Dagang Zhou, jinyuan wang, Panpan Zhou, huanwang jing
Highly efficient one-pot synthesis of imidazo[2,1-b]thiazole derivatives has been developed by a ring-opening and ring-closing reconstruction of imidazo[2,1-b][1,3,4]thiadiazoles with phenylacetylene in the presence of potassium tert-butoxide (t-BuOK) under very mild...
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Green organocatalytic [small alpha]-hydroxylation of ketones
DOI: 10.1039/C6OB00036C, PaperErrika Voutyritsa, Alexis Theodorou, Christoforos G. Kokotos
An efficient and green method for the [small alpha]-hydroxylation of substituted ketones has been developed.
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