Kirill Tchabanenko - Academia.edu (original) (raw)

Papers by Kirill Tchabanenko

Research paper thumbnail of Retraction of "Biomimetic Total Synthesis of Himbacine

Organic letters, Jan 19, 2015

Research paper thumbnail of Aryl Pyrrolidinones via Radical 1,4-Aryl Migration and 5-endo-trig Cyclization of N-(2-Bromoallyl)arylcarboxamides

Research paper thumbnail of ChemInform Abstract: Pyrrolidinone-Fused Cyclohexenones by Regioselective Dearomatizing Anionic Cyclization of 2-, 3-, or 4-Methoxybenzamides

Research paper thumbnail of Radical dearomatising spirocyclisations onto the C-2 position of benzofuran and indole

Tetrahedron Letters, 2004

Research paper thumbnail of Diastereoselective synthesis of 3,6-disubstituted 3,6-dihydropyridin-2-ones

Tetrahedron Letters, 2003

In a short sequence, 5-vinyloxazolidin-2-ones were converted into the 3,6-disubstituted 3,6-dihyd... more In a short sequence, 5-vinyloxazolidin-2-ones were converted into the 3,6-disubstituted 3,6-dihydropyridin-2-ones via Pd-catalysed carbonylation and enolate alkylation with high diastereoselectivity. Alkylation of 6-substituted N-methylpyridin-2-ones gives stereoselectively the 3,6-anti diastereoisomer with MeI, BuI and i-PrI. Alkylation of the corresponding N-BOC pyridinones gives the 3,6-syn diastereoisomer with high selectivity.

Research paper thumbnail of Aryl pyrrolidinones via radical 1,4-aryl migration and 5-endo-trig cyclisation of N-(2-bromoallyl)arylcarboxamides

Tetrahedron Letters, 2006

Radical reaction of a series of N-(2-bromoallyl)arylcarboxamides led to the production of 4-arylp... more Radical reaction of a series of N-(2-bromoallyl)arylcarboxamides led to the production of 4-arylpyrrolidin-2-ones and directly reduced materials in comparable yields. A cascade process, involving sequential 5-exo-trig spirocyclisation, β-scission, and 5-endo-trig ...

Research paper thumbnail of Synthesis of linked heterocycles via use of bis-acetylenic compounds

Tetrahedron Letters, 2006

... Full Text via CrossRef | View Record in Scopus | Cited By in Scopus (7). 2 MP Sammes, TF Lai,... more ... Full Text via CrossRef | View Record in Scopus | Cited By in Scopus (7). 2 MP Sammes, TF Lai, AR Katritzky, R. Murugan and H. Luce, J. Chem. Soc., Perkin Trans. ... 10 JS Yadav, BVS Reddy, KB Reddy, KU Gayathri and AR Prasad, Tetrahedron Lett. 44 (2003), p. 6493. ...

Research paper thumbnail of Rapid annulation of tropolone units via a pyrylium ylide 1,3-dipolar cycloaddition reaction

Tetrahedron Letters, 2010

The tropolone subunit of the naturally occurring alkaloid rubrolone aglycon is synthesized via a ... more The tropolone subunit of the naturally occurring alkaloid rubrolone aglycon is synthesized via a short reaction sequence starting with a 1,3-dipolar cycloaddition of a pyrylium ylide and indenone, followed by enone oxidation, oxygen-bridge elimination and finally hydroxy group oxidation.

Research paper thumbnail of Radical 1,4-aryl transfer in arylcarboxamides leading to phthalimides, biaryls and enantiomerically enriched β-arylethylamines

Tetrahedron, 2008

a b s t r a c t 5-exo Cyclisation of vinyl-, aryl-and alkyl-radicals onto the aryl group of arylc... more a b s t r a c t 5-exo Cyclisation of vinyl-, aryl-and alkyl-radicals onto the aryl group of arylcarboxamides is followed by b-scission of the resulting spirocyclohexadienyl radicals with ejection of a carbamoyl radical. The fate of this radical depends on the substrate but, in the cases studied, either 5-endo cyclisation or direct reduction follows to give phthalimides, biaryls or b-arylethylamines.

Research paper thumbnail of Biomimetic approach to Galbulimina type I alkaloids

Tetrahedron, 2005

Biomimetic Approach to Galbulimina Type I Alkaloids.

Research paper thumbnail of Oral 28-day and developmental toxicity studies of (R)-3-hydroxybutyl (R)-3-hydroxybutyrate

Regulatory Toxicology and Pharmacology, 2012

a b s t r a c t (R)-3-Hydroxybutyl (R)-3-hydroxybutyrate (ketone monoester) has been developed as... more a b s t r a c t (R)-3-Hydroxybutyl (R)-3-hydroxybutyrate (ketone monoester) has been developed as an oral source of ketones, which may be utilized for energy. In a 28-day toxicity study, Crl:WI (Wistar) rats received diets containing, as 30% of the calories, ketone monoester (12 and 15 g/kg body weight/day for male and female rats, respectively). Control groups received either carbohydrate-or fat-based diets. Rats in the test group consumed less feed and gained less weight than control animals; similar findings have been documented in studies of ketogenic diets. Between-group differences were noted in selected hematology, coagulation, and serum chemistry parameters; however, values were within normal physiological ranges and/or were not accompanied by other changes indicative of toxicity. Upon gross and microscopic evaluation, there were no findings associated with the ketone monoester. In a developmental toxicity study, pregnant Crl:WI (Han) rats were administered 2 g/kg body weight/day ketone monoester or water (control) via gavage on days 6 through 20 of gestation. No Caesarean-sectioning or litter parameters were affected by the test article. The overall incidence of fetal alterations was higher in the test group; however, there were no specific alterations attributable to the test substance. The results of these studies support the safety of ketone monoester.

Research paper thumbnail of Kinetics, safety and tolerability of (R)-3-hydroxybutyl (R)-3-hydroxybutyrate in healthy adult subjects

Regulatory Toxicology and Pharmacology, 2012

Induction of mild states of hyperketonemia may improve physical and cognitive performance. In thi... more Induction of mild states of hyperketonemia may improve physical and cognitive performance. In this study, we determined the kinetic parameters, safety and tolerability of (R)-3-hydroxybutyl (R)-3-hydroxybutyrate, a ketone monoester administered in the form of a meal replacement drink to healthy human volunteers. Plasma levels of -hydroxybutyrate and acetoacetate were elevated following administration of a single dose of the ketone monoester, whether at 140, 357, or 714 mg/kg body weight, while the intact ester was not detected. Maximum plasma levels of ketones were attained within 1-2 h, reaching 3.30 mM and 1.19 mM for -hydroxybutyrate and acetoacetate, respectively, at the highest dose tested. The elimination half-life ranged from 0.8-3.1 h for -hydroxybutyrate and 8-14 h for acetoacetate. The ketone monoester was also administered at 140, 357, and 714 mg/kg body weight, three times daily, over 5 days (equivalent to 0.42, 1.07, and 2.14 g/kg/d). The ketone ester was generally well-tolerated, although some gastrointestinal effects were reported, when large volumes of milk-based drink were consumed, at the highest ketone monoester dose. Together, these results suggest ingestion of (R)-3-hydroxybutyl (R)-3hydroxybutyrate is a safe and simple method to elevate blood ketone levels, compared with the inconvenience of preparing and consuming a ketogenic diet.

Research paper thumbnail of A Concise Approach to a Gelsemine Core Structure using an Oxygen to Carbon Bridge Swapping Strategy

Organic Letters, 2008

A tricyclic core structure 2 related to gelsemine 1 was synthesized from an oxabicyclo[3.2.1]octa... more A tricyclic core structure 2 related to gelsemine 1 was synthesized from an oxabicyclo[3.2.1]octanone 4 by a three-step bridge swapping strategy involving elimination of the bridging ether oxygen and intramolecular Michael addition of a tethered cyanoacetamide unit.

Research paper thumbnail of Biomimetic Total Synthesis of (+)-Himbacine

Organic Letters, 2005

On treatment with trifluoroacetic acid butenolide 14 undergoes N-Boc deprotection and condensatio... more On treatment with trifluoroacetic acid butenolide 14 undergoes N-Boc deprotection and condensation followed by an iminium ion activated intramolecular Diels-Alder cycloaddition to give the (+)-himbacine precursor 11 on reductive work up. Compound 11 was converted into (+)-himbacine in four synthetic steps. [reaction: see text]

Research paper thumbnail of New Domino Silyl Enol Ether Reactions in the Synthesis of a Tetrodecamycin Fragment

European Journal of Organic Chemistry, 2006

Research paper thumbnail of Biomimetic synthesis of the pyrrolobenzoxazine core of paeciloxazine

Chemical Communications, 2004

Starting from a protected L-tryptophan derivative the pyrrolobenzoxazine core unit of paeciloxazi... more Starting from a protected L-tryptophan derivative the pyrrolobenzoxazine core unit of paeciloxazine can be synthesized in two oxidation steps.

Research paper thumbnail of Synthesis of (±)-kainic acid by dearomatising cyclisation of a lithiated N-benzyl p-anisamide

Chemical Communications, 2000

... Jonathan Clayden* and Kirill Tchabanenko. Department of Chemistry, University of Manchester, ... more ... Jonathan Clayden* and Kirill Tchabanenko. Department of Chemistry, University of Manchester, Oxford Road, Manchester, UK M13 9PL ... 2171 Article ChemPort ; (s) J. Cossy, M. Cases and DG Pardo, Tetrahedron, 1999, 55, 6153 Article ChemPort ; (t) AD Campbell, TM Raynham ...

Research paper thumbnail of Mechanochemical synthesis of TiO2/NiFe2O4 magnetic catalysts for operation under RF field

Materials Science and Engineering: B, 2015

ABSTRACT Composite NiFe2O4–TiO2 magnetic catalysts were prepared by mechanochemical synthesis fro... more ABSTRACT Composite NiFe2O4–TiO2 magnetic catalysts were prepared by mechanochemical synthesis from a mixture of titania supported nickel ferrite nanoparticles and P25 titania (Evonic). The former provides fast and efficient heating under radiofrequency field, while the latter serves as an active catalyst or catalyst support. The highest heating rate was observed over a catalyst prepared for a milling time of 30 min. The catalytic activity was measured over the sulfated composite catalysts in condensation of aniline and 3-phenylbutyric acid in a stirred tank reactor and in a continuous RF heated flow reactor in the 140–170 °C range. The product yield of 47% was obtained over the sulfated P25 titania catalyst in the flow reactor.

Research paper thumbnail of Retraction of "Biomimetic Total Synthesis of Himbacine

Organic letters, Jan 19, 2015

Research paper thumbnail of Aryl Pyrrolidinones via Radical 1,4-Aryl Migration and 5-endo-trig Cyclization of N-(2-Bromoallyl)arylcarboxamides

Research paper thumbnail of ChemInform Abstract: Pyrrolidinone-Fused Cyclohexenones by Regioselective Dearomatizing Anionic Cyclization of 2-, 3-, or 4-Methoxybenzamides

Research paper thumbnail of Radical dearomatising spirocyclisations onto the C-2 position of benzofuran and indole

Tetrahedron Letters, 2004

Research paper thumbnail of Diastereoselective synthesis of 3,6-disubstituted 3,6-dihydropyridin-2-ones

Tetrahedron Letters, 2003

In a short sequence, 5-vinyloxazolidin-2-ones were converted into the 3,6-disubstituted 3,6-dihyd... more In a short sequence, 5-vinyloxazolidin-2-ones were converted into the 3,6-disubstituted 3,6-dihydropyridin-2-ones via Pd-catalysed carbonylation and enolate alkylation with high diastereoselectivity. Alkylation of 6-substituted N-methylpyridin-2-ones gives stereoselectively the 3,6-anti diastereoisomer with MeI, BuI and i-PrI. Alkylation of the corresponding N-BOC pyridinones gives the 3,6-syn diastereoisomer with high selectivity.

Research paper thumbnail of Aryl pyrrolidinones via radical 1,4-aryl migration and 5-endo-trig cyclisation of N-(2-bromoallyl)arylcarboxamides

Tetrahedron Letters, 2006

Radical reaction of a series of N-(2-bromoallyl)arylcarboxamides led to the production of 4-arylp... more Radical reaction of a series of N-(2-bromoallyl)arylcarboxamides led to the production of 4-arylpyrrolidin-2-ones and directly reduced materials in comparable yields. A cascade process, involving sequential 5-exo-trig spirocyclisation, β-scission, and 5-endo-trig ...

Research paper thumbnail of Synthesis of linked heterocycles via use of bis-acetylenic compounds

Tetrahedron Letters, 2006

... Full Text via CrossRef | View Record in Scopus | Cited By in Scopus (7). 2 MP Sammes, TF Lai,... more ... Full Text via CrossRef | View Record in Scopus | Cited By in Scopus (7). 2 MP Sammes, TF Lai, AR Katritzky, R. Murugan and H. Luce, J. Chem. Soc., Perkin Trans. ... 10 JS Yadav, BVS Reddy, KB Reddy, KU Gayathri and AR Prasad, Tetrahedron Lett. 44 (2003), p. 6493. ...

Research paper thumbnail of Rapid annulation of tropolone units via a pyrylium ylide 1,3-dipolar cycloaddition reaction

Tetrahedron Letters, 2010

The tropolone subunit of the naturally occurring alkaloid rubrolone aglycon is synthesized via a ... more The tropolone subunit of the naturally occurring alkaloid rubrolone aglycon is synthesized via a short reaction sequence starting with a 1,3-dipolar cycloaddition of a pyrylium ylide and indenone, followed by enone oxidation, oxygen-bridge elimination and finally hydroxy group oxidation.

Research paper thumbnail of Radical 1,4-aryl transfer in arylcarboxamides leading to phthalimides, biaryls and enantiomerically enriched β-arylethylamines

Tetrahedron, 2008

a b s t r a c t 5-exo Cyclisation of vinyl-, aryl-and alkyl-radicals onto the aryl group of arylc... more a b s t r a c t 5-exo Cyclisation of vinyl-, aryl-and alkyl-radicals onto the aryl group of arylcarboxamides is followed by b-scission of the resulting spirocyclohexadienyl radicals with ejection of a carbamoyl radical. The fate of this radical depends on the substrate but, in the cases studied, either 5-endo cyclisation or direct reduction follows to give phthalimides, biaryls or b-arylethylamines.

Research paper thumbnail of Biomimetic approach to Galbulimina type I alkaloids

Tetrahedron, 2005

Biomimetic Approach to Galbulimina Type I Alkaloids.

Research paper thumbnail of Oral 28-day and developmental toxicity studies of (R)-3-hydroxybutyl (R)-3-hydroxybutyrate

Regulatory Toxicology and Pharmacology, 2012

a b s t r a c t (R)-3-Hydroxybutyl (R)-3-hydroxybutyrate (ketone monoester) has been developed as... more a b s t r a c t (R)-3-Hydroxybutyl (R)-3-hydroxybutyrate (ketone monoester) has been developed as an oral source of ketones, which may be utilized for energy. In a 28-day toxicity study, Crl:WI (Wistar) rats received diets containing, as 30% of the calories, ketone monoester (12 and 15 g/kg body weight/day for male and female rats, respectively). Control groups received either carbohydrate-or fat-based diets. Rats in the test group consumed less feed and gained less weight than control animals; similar findings have been documented in studies of ketogenic diets. Between-group differences were noted in selected hematology, coagulation, and serum chemistry parameters; however, values were within normal physiological ranges and/or were not accompanied by other changes indicative of toxicity. Upon gross and microscopic evaluation, there were no findings associated with the ketone monoester. In a developmental toxicity study, pregnant Crl:WI (Han) rats were administered 2 g/kg body weight/day ketone monoester or water (control) via gavage on days 6 through 20 of gestation. No Caesarean-sectioning or litter parameters were affected by the test article. The overall incidence of fetal alterations was higher in the test group; however, there were no specific alterations attributable to the test substance. The results of these studies support the safety of ketone monoester.

Research paper thumbnail of Kinetics, safety and tolerability of (R)-3-hydroxybutyl (R)-3-hydroxybutyrate in healthy adult subjects

Regulatory Toxicology and Pharmacology, 2012

Induction of mild states of hyperketonemia may improve physical and cognitive performance. In thi... more Induction of mild states of hyperketonemia may improve physical and cognitive performance. In this study, we determined the kinetic parameters, safety and tolerability of (R)-3-hydroxybutyl (R)-3-hydroxybutyrate, a ketone monoester administered in the form of a meal replacement drink to healthy human volunteers. Plasma levels of -hydroxybutyrate and acetoacetate were elevated following administration of a single dose of the ketone monoester, whether at 140, 357, or 714 mg/kg body weight, while the intact ester was not detected. Maximum plasma levels of ketones were attained within 1-2 h, reaching 3.30 mM and 1.19 mM for -hydroxybutyrate and acetoacetate, respectively, at the highest dose tested. The elimination half-life ranged from 0.8-3.1 h for -hydroxybutyrate and 8-14 h for acetoacetate. The ketone monoester was also administered at 140, 357, and 714 mg/kg body weight, three times daily, over 5 days (equivalent to 0.42, 1.07, and 2.14 g/kg/d). The ketone ester was generally well-tolerated, although some gastrointestinal effects were reported, when large volumes of milk-based drink were consumed, at the highest ketone monoester dose. Together, these results suggest ingestion of (R)-3-hydroxybutyl (R)-3hydroxybutyrate is a safe and simple method to elevate blood ketone levels, compared with the inconvenience of preparing and consuming a ketogenic diet.

Research paper thumbnail of A Concise Approach to a Gelsemine Core Structure using an Oxygen to Carbon Bridge Swapping Strategy

Organic Letters, 2008

A tricyclic core structure 2 related to gelsemine 1 was synthesized from an oxabicyclo[3.2.1]octa... more A tricyclic core structure 2 related to gelsemine 1 was synthesized from an oxabicyclo[3.2.1]octanone 4 by a three-step bridge swapping strategy involving elimination of the bridging ether oxygen and intramolecular Michael addition of a tethered cyanoacetamide unit.

Research paper thumbnail of Biomimetic Total Synthesis of (+)-Himbacine

Organic Letters, 2005

On treatment with trifluoroacetic acid butenolide 14 undergoes N-Boc deprotection and condensatio... more On treatment with trifluoroacetic acid butenolide 14 undergoes N-Boc deprotection and condensation followed by an iminium ion activated intramolecular Diels-Alder cycloaddition to give the (+)-himbacine precursor 11 on reductive work up. Compound 11 was converted into (+)-himbacine in four synthetic steps. [reaction: see text]

Research paper thumbnail of New Domino Silyl Enol Ether Reactions in the Synthesis of a Tetrodecamycin Fragment

European Journal of Organic Chemistry, 2006

Research paper thumbnail of Biomimetic synthesis of the pyrrolobenzoxazine core of paeciloxazine

Chemical Communications, 2004

Starting from a protected L-tryptophan derivative the pyrrolobenzoxazine core unit of paeciloxazi... more Starting from a protected L-tryptophan derivative the pyrrolobenzoxazine core unit of paeciloxazine can be synthesized in two oxidation steps.

Research paper thumbnail of Synthesis of (±)-kainic acid by dearomatising cyclisation of a lithiated N-benzyl p-anisamide

Chemical Communications, 2000

... Jonathan Clayden* and Kirill Tchabanenko. Department of Chemistry, University of Manchester, ... more ... Jonathan Clayden* and Kirill Tchabanenko. Department of Chemistry, University of Manchester, Oxford Road, Manchester, UK M13 9PL ... 2171 Article ChemPort ; (s) J. Cossy, M. Cases and DG Pardo, Tetrahedron, 1999, 55, 6153 Article ChemPort ; (t) AD Campbell, TM Raynham ...

Research paper thumbnail of Mechanochemical synthesis of TiO2/NiFe2O4 magnetic catalysts for operation under RF field

Materials Science and Engineering: B, 2015

ABSTRACT Composite NiFe2O4–TiO2 magnetic catalysts were prepared by mechanochemical synthesis fro... more ABSTRACT Composite NiFe2O4–TiO2 magnetic catalysts were prepared by mechanochemical synthesis from a mixture of titania supported nickel ferrite nanoparticles and P25 titania (Evonic). The former provides fast and efficient heating under radiofrequency field, while the latter serves as an active catalyst or catalyst support. The highest heating rate was observed over a catalyst prepared for a milling time of 30 min. The catalytic activity was measured over the sulfated composite catalysts in condensation of aniline and 3-phenylbutyric acid in a stirred tank reactor and in a continuous RF heated flow reactor in the 140–170 °C range. The product yield of 47% was obtained over the sulfated P25 titania catalyst in the flow reactor.