Sylvain Collet - Academia.edu (original) (raw)

Papers by Sylvain Collet

Research paper thumbnail of A regioselective C7 bromination and C7 palladium-catalyzed Suzuki–Miyaura cross-coupling arylation of 4-substituted NH-free indazoles

RSC Advances

A regioselective C7-bromination of 4-substituted 1H-indazoles followed by a palladium-catalyzed S... more A regioselective C7-bromination of 4-substituted 1H-indazoles followed by a palladium-catalyzed Suzuki–Miyaura reaction with boronic acids is described.

Research paper thumbnail of Stereospecific C-Glycosylation by Mizoroki-Heck Reaction: A Powerful and Easy-to-Set-Up Synthetic Tool to Access α - and β -Aryl-C -Glycosides

Chemistry - A European Journal

A stereospecific Mizoroki-Heck cross-coupling of differently substituted glycals with haloarenes ... more A stereospecific Mizoroki-Heck cross-coupling of differently substituted glycals with haloarenes resulting in the exclusive formation of either  or  aryl-C-glycosides depending solely on the [a]

Research paper thumbnail of Stereodivergent approach in the protected glycal synthesis of L-vancosamine, L-saccharosamine, L-daunosamine and L-ristosamine involving a ring-closing metathesis step

Beilstein Journal of Organic Chemistry

In this paper, a new access to several chiral 3-aminoglycals as potential precursors for glycosyl... more In this paper, a new access to several chiral 3-aminoglycals as potential precursors for glycosylated natural products is reported from a common starting material, (−)-methyl-L-lactate. The stereodivergent strategy is based on the implementation of a ring-closing metathesis of vinyl ethers as key step of reaction sequences developed.

Research paper thumbnail of Total Synthesis of γ-Indomycinone and Kidamycinone by Means of Two Regioselective Diels-Alder Reactions

The Journal of organic chemistry, Jan 2, 2017

An efficient access for the synthesis of pluramycinones is described. Total syntheses of racemic ... more An efficient access for the synthesis of pluramycinones is described. Total syntheses of racemic γ-indomycinone and kidamycinone were achieved by means of two Diels-Alder reactions. A first Diels-Alder condensation followed by a Stille cross-coupling is used for the elaboration of the desired substituted dienes which will be involved in the second pericyclic reaction with juglone to construct the tetracyclic core of pluramycinones.

Research paper thumbnail of ChemInform Abstract: Suzuki Cross-Coupling Reactions of Nonracemic Vinylborono-a-amino Acids

Cheminform, 2010

Suzuki Cross-Coupling Reactions of Nonracemic Vinylborono-αamino Acids.-Vinylborono-α-amino acids... more Suzuki Cross-Coupling Reactions of Nonracemic Vinylborono-αamino Acids.-Vinylborono-α-amino acids (I) and (IV) undergo Suzuki coupling with vinylic or aromatic bromides (II), allowing an easy access to stereodefined unsaturated nonproteinogenic α-amino acids (III) and (V). Using cesium fluoride as a base, the protective groups are not affected.-(COLLET,

Research paper thumbnail of Stereoselective, nonracemic synthesis of ?-borono-a-amino acids

Tetrahedron Asymmetry, 1998

Research paper thumbnail of Enantioselective Synthesis of an Advanced Intermediate for the Synthesis of Brefeldin A and Analogues

Synlett, Feb 1, 2008

ABSTRACT A synthesis of methyl (1R,2R,4S)-2-[(E)-2-iodovinyl]-4-(methoxymethoxy)cyclopentanecarbo... more ABSTRACT A synthesis of methyl (1R,2R,4S)-2-[(E)-2-iodovinyl]-4-(methoxymethoxy)cyclopentanecarboxylate is described in nine steps from a prochiral anhydride. A desymmetrization reaction followed by an epimerization and a Takai reaction are the key steps of the transformation. Based on previous work, this vinylic iodide product should be a useful precursor for the synthesis of brefeldin A and analogues.

Research paper thumbnail of Practical Synthesis of ( S )-1-(3-Trifluoromethylphenyl)ethanol via Ruthenium(II)-catalyzed Asymmetric Transfer Hydrogenation

Organic Process Research & Development, 2000

... Hydrogenation of a β-Enamine Amide. Andrew M. Clausen, Brianne Dziadul, Kristine L. Cappuccio... more ... Hydrogenation of a β-Enamine Amide. Andrew M. Clausen, Brianne Dziadul, Kristine L. Cappuccio, Mahmoud Kaba, Cindy Starbuck, Yi Hsiao, and Thomas M. Dowling. Organic Process Research & Development 2006 10 (4), pp 723–726. ...

Research paper thumbnail of ChemInform Abstract: A New Enlargement Methodology for the Preparation of 2H-1- and 2H-3-Benzazepin-2-one Derivatives

Research paper thumbnail of Synthesis of chiral N-protected 1,2-dihydro-quinoline-2-carbonitrile and 1,2-dihydro-isoquinoline-1-carbonitrile via an asymmetric Reissert reaction

Tetrahedron Letters, 2005

Addition of cyanide ion to chiral N-acyl-quinolinium and N-acyl-isoquinolinium salts led selectiv... more Addition of cyanide ion to chiral N-acyl-quinolinium and N-acyl-isoquinolinium salts led selectively to 1,2-addition products. Removal of the chiral auxiliary affords the title compounds in pure enantiomeric form.

Research paper thumbnail of Total synthesis of (±)-γ-indomycinone

Tetrahedron Letters, 2015

Research paper thumbnail of Synthesis and evaluation of ω-borono-α-amino acids † as active-site probes of arginase and nitric oxide synthases

Journal of the Chemical Society, Perkin Transactions 1, 2000

J. Chem. Soc., Perkin Trans. 1, 2000, 177-182 DOI:10.1039/A908140B (Paper). Synthesis and evaluat... more J. Chem. Soc., Perkin Trans. 1, 2000, 177-182 DOI:10.1039/A908140B (Paper). Synthesis and evaluation of ω-borono-α-amino acids † as active-site probes of arginase and nitric oxide synthases. Sylvain Colleta, François Carreaux ...

Research paper thumbnail of ChemInform Abstract: Synthesis and Evaluation of ω-Borono-α-Amino Acids as Active-Site Probes of Arginase and Nitric Oxide Synthases

Research paper thumbnail of ChemInform Abstract: Suzuki Cross-Coupling Reactions of Nonracemic Vinylborono-α-amino Acids

ChemInform, 2001

Suzuki cross-coupling reaction between phenyl bromide and phenylboronic acid, catalyzed by the pa... more Suzuki cross-coupling reaction between phenyl bromide and phenylboronic acid, catalyzed by the palladium complex Pd[N-MorphC(S)NP(O)(OiPr) 2-1,5-O,S)] 2 in acetonitrile, toluene, THF or DMF has been investigated. Bases employed for the reaction were Na 2 CO 3 , K 2 CO 3 or Cs 2 CO 3. Varying largely the experimental conditions we found that excellent yields of the product were obtained using toluene and K 2 CO 3 at 100°C at the catalyst amount of 0.02 mmol.

Research paper thumbnail of ChemInform Abstract: Stereoselective, Nonracemic Synthesis of ω-Borono-α-amino Acids

Research paper thumbnail of A Synthesis of Calothrixin B

Research paper thumbnail of ChemInform Abstract: A Diels-Alder Approach to Anthrapyran Antibiotics

ChemInform, 2012

ABSTRACT Pyran synthons (II) and (IV) are used in the cycloadditions of naphthoquinones (I) which... more ABSTRACT Pyran synthons (II) and (IV) are used in the cycloadditions of naphthoquinones (I) which afford the pluramycin framework in a completely diastereoselective manner.

Research paper thumbnail of tert -Butyl Carbamate

Encyclopedia of Reagents for Organic Synthesis, 2001

Research paper thumbnail of ChemInform Abstract: A New Synthesis of (R)-(-)-Sumanirole (PNU-95666E)

ChemInform, 2010

ABSTRACT The title compound (VI) was investigated in clinical studies for the treatment of Parkin... more ABSTRACT The title compound (VI) was investigated in clinical studies for the treatment of Parkinson′s disease and found to be unsuitable.

Research paper thumbnail of Stereoselective, nonracemic synthesis of ω-borono-α-amino acids

Tetrahedron: Asymmetry, 1998

ω-Unsaturated α-amino acids are synthesized through condensation of allyl and propargyl bromides ... more ω-Unsaturated α-amino acids are synthesized through condensation of allyl and propargyl bromides or of 9bromoundecene with a Ni(II) complex of the Schiff base derived from glycine and BPB. Hydroboration with Ipc 2 BH followed by oxidation with acetaldehyde affords enantiomerically pure ω-borono-α-aminocarboxylic acids.

Research paper thumbnail of A regioselective C7 bromination and C7 palladium-catalyzed Suzuki–Miyaura cross-coupling arylation of 4-substituted NH-free indazoles

RSC Advances

A regioselective C7-bromination of 4-substituted 1H-indazoles followed by a palladium-catalyzed S... more A regioselective C7-bromination of 4-substituted 1H-indazoles followed by a palladium-catalyzed Suzuki–Miyaura reaction with boronic acids is described.

Research paper thumbnail of Stereospecific C-Glycosylation by Mizoroki-Heck Reaction: A Powerful and Easy-to-Set-Up Synthetic Tool to Access α - and β -Aryl-C -Glycosides

Chemistry - A European Journal

A stereospecific Mizoroki-Heck cross-coupling of differently substituted glycals with haloarenes ... more A stereospecific Mizoroki-Heck cross-coupling of differently substituted glycals with haloarenes resulting in the exclusive formation of either  or  aryl-C-glycosides depending solely on the [a]

Research paper thumbnail of Stereodivergent approach in the protected glycal synthesis of L-vancosamine, L-saccharosamine, L-daunosamine and L-ristosamine involving a ring-closing metathesis step

Beilstein Journal of Organic Chemistry

In this paper, a new access to several chiral 3-aminoglycals as potential precursors for glycosyl... more In this paper, a new access to several chiral 3-aminoglycals as potential precursors for glycosylated natural products is reported from a common starting material, (−)-methyl-L-lactate. The stereodivergent strategy is based on the implementation of a ring-closing metathesis of vinyl ethers as key step of reaction sequences developed.

Research paper thumbnail of Total Synthesis of γ-Indomycinone and Kidamycinone by Means of Two Regioselective Diels-Alder Reactions

The Journal of organic chemistry, Jan 2, 2017

An efficient access for the synthesis of pluramycinones is described. Total syntheses of racemic ... more An efficient access for the synthesis of pluramycinones is described. Total syntheses of racemic γ-indomycinone and kidamycinone were achieved by means of two Diels-Alder reactions. A first Diels-Alder condensation followed by a Stille cross-coupling is used for the elaboration of the desired substituted dienes which will be involved in the second pericyclic reaction with juglone to construct the tetracyclic core of pluramycinones.

Research paper thumbnail of ChemInform Abstract: Suzuki Cross-Coupling Reactions of Nonracemic Vinylborono-a-amino Acids

Cheminform, 2010

Suzuki Cross-Coupling Reactions of Nonracemic Vinylborono-αamino Acids.-Vinylborono-α-amino acids... more Suzuki Cross-Coupling Reactions of Nonracemic Vinylborono-αamino Acids.-Vinylborono-α-amino acids (I) and (IV) undergo Suzuki coupling with vinylic or aromatic bromides (II), allowing an easy access to stereodefined unsaturated nonproteinogenic α-amino acids (III) and (V). Using cesium fluoride as a base, the protective groups are not affected.-(COLLET,

Research paper thumbnail of Stereoselective, nonracemic synthesis of ?-borono-a-amino acids

Tetrahedron Asymmetry, 1998

Research paper thumbnail of Enantioselective Synthesis of an Advanced Intermediate for the Synthesis of Brefeldin A and Analogues

Synlett, Feb 1, 2008

ABSTRACT A synthesis of methyl (1R,2R,4S)-2-[(E)-2-iodovinyl]-4-(methoxymethoxy)cyclopentanecarbo... more ABSTRACT A synthesis of methyl (1R,2R,4S)-2-[(E)-2-iodovinyl]-4-(methoxymethoxy)cyclopentanecarboxylate is described in nine steps from a prochiral anhydride. A desymmetrization reaction followed by an epimerization and a Takai reaction are the key steps of the transformation. Based on previous work, this vinylic iodide product should be a useful precursor for the synthesis of brefeldin A and analogues.

Research paper thumbnail of Practical Synthesis of ( S )-1-(3-Trifluoromethylphenyl)ethanol via Ruthenium(II)-catalyzed Asymmetric Transfer Hydrogenation

Organic Process Research & Development, 2000

... Hydrogenation of a β-Enamine Amide. Andrew M. Clausen, Brianne Dziadul, Kristine L. Cappuccio... more ... Hydrogenation of a β-Enamine Amide. Andrew M. Clausen, Brianne Dziadul, Kristine L. Cappuccio, Mahmoud Kaba, Cindy Starbuck, Yi Hsiao, and Thomas M. Dowling. Organic Process Research & Development 2006 10 (4), pp 723–726. ...

Research paper thumbnail of ChemInform Abstract: A New Enlargement Methodology for the Preparation of 2H-1- and 2H-3-Benzazepin-2-one Derivatives

Research paper thumbnail of Synthesis of chiral N-protected 1,2-dihydro-quinoline-2-carbonitrile and 1,2-dihydro-isoquinoline-1-carbonitrile via an asymmetric Reissert reaction

Tetrahedron Letters, 2005

Addition of cyanide ion to chiral N-acyl-quinolinium and N-acyl-isoquinolinium salts led selectiv... more Addition of cyanide ion to chiral N-acyl-quinolinium and N-acyl-isoquinolinium salts led selectively to 1,2-addition products. Removal of the chiral auxiliary affords the title compounds in pure enantiomeric form.

Research paper thumbnail of Total synthesis of (±)-γ-indomycinone

Tetrahedron Letters, 2015

Research paper thumbnail of Synthesis and evaluation of ω-borono-α-amino acids † as active-site probes of arginase and nitric oxide synthases

Journal of the Chemical Society, Perkin Transactions 1, 2000

J. Chem. Soc., Perkin Trans. 1, 2000, 177-182 DOI:10.1039/A908140B (Paper). Synthesis and evaluat... more J. Chem. Soc., Perkin Trans. 1, 2000, 177-182 DOI:10.1039/A908140B (Paper). Synthesis and evaluation of ω-borono-α-amino acids † as active-site probes of arginase and nitric oxide synthases. Sylvain Colleta, François Carreaux ...

Research paper thumbnail of ChemInform Abstract: Synthesis and Evaluation of ω-Borono-α-Amino Acids as Active-Site Probes of Arginase and Nitric Oxide Synthases

Research paper thumbnail of ChemInform Abstract: Suzuki Cross-Coupling Reactions of Nonracemic Vinylborono-α-amino Acids

ChemInform, 2001

Suzuki cross-coupling reaction between phenyl bromide and phenylboronic acid, catalyzed by the pa... more Suzuki cross-coupling reaction between phenyl bromide and phenylboronic acid, catalyzed by the palladium complex Pd[N-MorphC(S)NP(O)(OiPr) 2-1,5-O,S)] 2 in acetonitrile, toluene, THF or DMF has been investigated. Bases employed for the reaction were Na 2 CO 3 , K 2 CO 3 or Cs 2 CO 3. Varying largely the experimental conditions we found that excellent yields of the product were obtained using toluene and K 2 CO 3 at 100°C at the catalyst amount of 0.02 mmol.

Research paper thumbnail of ChemInform Abstract: Stereoselective, Nonracemic Synthesis of ω-Borono-α-amino Acids

Research paper thumbnail of A Synthesis of Calothrixin B

Research paper thumbnail of ChemInform Abstract: A Diels-Alder Approach to Anthrapyran Antibiotics

ChemInform, 2012

ABSTRACT Pyran synthons (II) and (IV) are used in the cycloadditions of naphthoquinones (I) which... more ABSTRACT Pyran synthons (II) and (IV) are used in the cycloadditions of naphthoquinones (I) which afford the pluramycin framework in a completely diastereoselective manner.

Research paper thumbnail of tert -Butyl Carbamate

Encyclopedia of Reagents for Organic Synthesis, 2001

Research paper thumbnail of ChemInform Abstract: A New Synthesis of (R)-(-)-Sumanirole (PNU-95666E)

ChemInform, 2010

ABSTRACT The title compound (VI) was investigated in clinical studies for the treatment of Parkin... more ABSTRACT The title compound (VI) was investigated in clinical studies for the treatment of Parkinson′s disease and found to be unsuitable.

Research paper thumbnail of Stereoselective, nonracemic synthesis of ω-borono-α-amino acids

Tetrahedron: Asymmetry, 1998

ω-Unsaturated α-amino acids are synthesized through condensation of allyl and propargyl bromides ... more ω-Unsaturated α-amino acids are synthesized through condensation of allyl and propargyl bromides or of 9bromoundecene with a Ni(II) complex of the Schiff base derived from glycine and BPB. Hydroboration with Ipc 2 BH followed by oxidation with acetaldehyde affords enantiomerically pure ω-borono-α-aminocarboxylic acids.