Jean-michel Vatèle - Academia.edu (original) (raw)
Papers by Jean-michel Vatèle
Journal of Biological Chemistry
Oxygen free radicals oxidize arachidonic acid to a complex mixture of metabolites termed isoeicos... more Oxygen free radicals oxidize arachidonic acid to a complex mixture of metabolites termed isoeicosanoids that share structural similarity to enzymatically derived eicosanoids. However, little is known about oxidations of arachidonic acid mediated by reactive radical nitrogen oxides. We have studied the reaction of arachidonic acid with NO2, a free radical generated by nitric oxide and nitrite oxidations. A major group of products appeared to be a mixture of arachidonic acid isomers having onetrans-bond and three cis-double bonds. We have termed these new products trans-arachidonic acids. These isomers were chromatographically distinct from arachidonic acid and produced mass spectra that were nearly identical with mass spectra of arachidonic acid. The lack of ultraviolet absorbance above 205 nm and the similarity of mass spectra of dimethyloxazoline derivatives suggested that the trans-bond was not conjugated with any of the cis-bonds, and the C=C bonds were located at carbons 5, 8, 1...
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Trans polyunsaturated fatty acids are produced in vegetable oils during heat treatment (240-250 °... more Trans polyunsaturated fatty acids are produced in vegetable oils during heat treatment (240-250 °C).ln order to study the metabolic pathway of 9c, 12t and 9t, 12c linoleic acid and 9c, 12c, 15t and 9t, 12c, 15c linolenic acid, these products were prepared labelled with carbon 14 in the carboxylic position. 5c, 8c, 11c, 14t-Arachidonic acid was also labelled on the carboxylic position with carbon 14 in order to study its physiological effects. To introduce the labelling (E)-bromo precursors with a 17 carbons chain or a 19 carbon chain were needed. The different syntheses were done by elongation steps and creation of cis double bonds via highly stereospecific Wittig reactions. The radioactive carbon atom was introduced from [14C]-potassium cyanide. The final radioactive fatty acids had a specific activity greater than 50 mCi/mmol and a radioactive purity better than 99 % for linoleic and linolenic and better than 98.6 % for arachidonic acid.
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Tetrahedron
A novel route to enantioenriched (+)-goniodiol and its natural acetylated derivatives, potent cyt... more A novel route to enantioenriched (+)-goniodiol and its natural acetylated derivatives, potent cytotoxic compounds, is described. The main features of this synthesis are transfer of the asymmetric information of the scalemic allenic alcohol 5 to the α- and β- carbons through highly diastereoselective reactions and introduction of the α,β-unsaturated lactone moiety by the Ghosez' methodology.
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ChemInform, 2011
ABSTRACT A sequential one-pot synthesis for the oxidation of primary and secondary tert-butyldime... more ABSTRACT A sequential one-pot synthesis for the oxidation of primary and secondary tert-butyldimethylsilyl (TBDMS) ethers, using catalytic amounts of metal triflates and TEMPO in combination with PhIO or PhI(OAc)(2) in THF or acetonitrile, is described. Acid-sensitive protecting groups such as methylidene, isopropylidene, acetals, and Boc are unaffected under the reaction conditions. Another feature of this procedure is its high selectivity for TBDMS ethers over tert-butyldiphenylsilyl ethers and of aliphatic TBDMS groups over phenolic TBDMS groups.
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Tetrahedron, 2012
ABSTRACT Our efforts in construction the 1,2-dioxane ring of plakortolides through two approaches... more ABSTRACT Our efforts in construction the 1,2-dioxane ring of plakortolides through two approaches are described. The first one involved as a key step an acid catalyzed 6-endo ring closure of b-hydroperoxy trans-epoxides directed by a vinyl group adjacent to the epoxide function. By this route, an advanced intermediate of plakortolides was obtained in six steps and 35% overall yield. The second approach featured a 1,2-dioxane ring forming by a double opening of bis-epoxides by ethereal hydrogen peroxide. This reaction did not proceed in the expected sense and exclusive formation of hydroperoxy tetrahydropyran derivatives was observed via a tandem oxacyclizationehydroperoxidation sequence.
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Tetrahedron Letters, 1996
... 1994, 35, 46854688 ; (b) Shing, TKM ; Tai, VWF ; Tsui, HCJ Chem. Soc. ... Chem. Int. Ed. Engl... more ... 1994, 35, 46854688 ; (b) Shing, TKM ; Tai, VWF ; Tsui, HCJ Chem. Soc. ... Chem. Int. Ed. Engl. 1980, 19, 557 558. 9. (a) Cha, JK ; Christ, WJ ; Kishi, Y. Tetrahedron 1984, 40, 22472255 ; (b) Oishi, T. ; Iida; KY ; Hirama, M. Tetrahedron Lett. 1993, 34, 35733576. 10. ...
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ChemInform, 2000
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ChemInform, 1999
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Biochimica et Biophysica Acta (BBA) - Lipids and Lipid Metabolism, 1998
Trans polyunsaturated fatty acids are formed during processing of vegetable oils such as deodoriz... more Trans polyunsaturated fatty acids are formed during processing of vegetable oils such as deodorization and frying.The oxidative metabolism of linoleic and α-linolenic acids and of their mono-trans isomers (9cis,12trans-18:2, 9trans,12cis-18:2 and 9cis,12cis,15trans-18:3, 9trans,12cis,15cis-18:3, respectively) was studied in fasting rats. A single dose of 18.5MBq of each [1-14C] labelled fatty acid (260μg) was orally given to the animals. The 14CO2 expired
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Tetrahedron Letters, 1999
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Tetrahedron, 1996
γ-butyrolactones are obtained in good yields from 4-trimethylsilyl-3-alkyn-1-ols via Wacker-type ... more γ-butyrolactones are obtained in good yields from 4-trimethylsilyl-3-alkyn-1-ols via Wacker-type oxidation reaction. A mechanism is proposed for this transformation: it involves two successive trans-hydroxypalladations followed by a [PdXSiMe3] syn-elimination and explains why the presence of the silyl group is essential in such a process.
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ChemInform, 1999
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ChemInform, 2000
ABSTRACT ChemInform is a weekly Abstracting Service, delivering concise information at a glance t... more ABSTRACT ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.
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ChemInform, 1999
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Tetrahedron Letters, 1996
... All fights reserved 00404039 96 15.00 + 0.00 Total Synthesis of (+)Goniodiol JeanPhilippe Sur... more ... All fights reserved 00404039 96 15.00 + 0.00 Total Synthesis of (+)Goniodiol JeanPhilippe Surivet,Jacques Gor and JeanMichel Vatle* Laboratoire de Chimie Organique 1, associ au CNRS, Universit ... 15. Ley, SV ; Norman, J. ; Griffith, WP ; Marsden, SP Synthesis 1994, 639666. ...
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Tetrahedron: Asymmetry, 1996
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Tetrahedron: Asymmetry, 1998
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Tetrahedron Letters, 1997
Synthesis of enantiopure (+)-7-epi-goniofufurone, 1 and (+)-goniopypyrone 2 has been achieved fro... more Synthesis of enantiopure (+)-7-epi-goniofufurone, 1 and (+)-goniopypyrone 2 has been achieved from C-4 carbon chain chiron 3, readily available from (R)-mandelic acid.
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Tetrahedron Letters, 1998
(+)-Goniodiol 7 and (+)-9-deoxygoniopypyrone 8, belonging to the group of styryllactones, have be... more (+)-Goniodiol 7 and (+)-9-deoxygoniopypyrone 8, belonging to the group of styryllactones, have been synthesized in five steps and 75% yield respectively from C4-esters 1a and 1b. The key step of these syntheses is a triflate-sulfone coupling which allowed a rapid construction of the backbone of the title compounds as well as the efficient installation of a masked Z-acrylate moiety.
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Tetrahedron Letters, 1999
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Journal of Biological Chemistry
Oxygen free radicals oxidize arachidonic acid to a complex mixture of metabolites termed isoeicos... more Oxygen free radicals oxidize arachidonic acid to a complex mixture of metabolites termed isoeicosanoids that share structural similarity to enzymatically derived eicosanoids. However, little is known about oxidations of arachidonic acid mediated by reactive radical nitrogen oxides. We have studied the reaction of arachidonic acid with NO2, a free radical generated by nitric oxide and nitrite oxidations. A major group of products appeared to be a mixture of arachidonic acid isomers having onetrans-bond and three cis-double bonds. We have termed these new products trans-arachidonic acids. These isomers were chromatographically distinct from arachidonic acid and produced mass spectra that were nearly identical with mass spectra of arachidonic acid. The lack of ultraviolet absorbance above 205 nm and the similarity of mass spectra of dimethyloxazoline derivatives suggested that the trans-bond was not conjugated with any of the cis-bonds, and the C=C bonds were located at carbons 5, 8, 1...
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Trans polyunsaturated fatty acids are produced in vegetable oils during heat treatment (240-250 °... more Trans polyunsaturated fatty acids are produced in vegetable oils during heat treatment (240-250 °C).ln order to study the metabolic pathway of 9c, 12t and 9t, 12c linoleic acid and 9c, 12c, 15t and 9t, 12c, 15c linolenic acid, these products were prepared labelled with carbon 14 in the carboxylic position. 5c, 8c, 11c, 14t-Arachidonic acid was also labelled on the carboxylic position with carbon 14 in order to study its physiological effects. To introduce the labelling (E)-bromo precursors with a 17 carbons chain or a 19 carbon chain were needed. The different syntheses were done by elongation steps and creation of cis double bonds via highly stereospecific Wittig reactions. The radioactive carbon atom was introduced from [14C]-potassium cyanide. The final radioactive fatty acids had a specific activity greater than 50 mCi/mmol and a radioactive purity better than 99 % for linoleic and linolenic and better than 98.6 % for arachidonic acid.
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Tetrahedron
A novel route to enantioenriched (+)-goniodiol and its natural acetylated derivatives, potent cyt... more A novel route to enantioenriched (+)-goniodiol and its natural acetylated derivatives, potent cytotoxic compounds, is described. The main features of this synthesis are transfer of the asymmetric information of the scalemic allenic alcohol 5 to the α- and β- carbons through highly diastereoselective reactions and introduction of the α,β-unsaturated lactone moiety by the Ghosez' methodology.
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ChemInform, 2011
ABSTRACT A sequential one-pot synthesis for the oxidation of primary and secondary tert-butyldime... more ABSTRACT A sequential one-pot synthesis for the oxidation of primary and secondary tert-butyldimethylsilyl (TBDMS) ethers, using catalytic amounts of metal triflates and TEMPO in combination with PhIO or PhI(OAc)(2) in THF or acetonitrile, is described. Acid-sensitive protecting groups such as methylidene, isopropylidene, acetals, and Boc are unaffected under the reaction conditions. Another feature of this procedure is its high selectivity for TBDMS ethers over tert-butyldiphenylsilyl ethers and of aliphatic TBDMS groups over phenolic TBDMS groups.
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Tetrahedron, 2012
ABSTRACT Our efforts in construction the 1,2-dioxane ring of plakortolides through two approaches... more ABSTRACT Our efforts in construction the 1,2-dioxane ring of plakortolides through two approaches are described. The first one involved as a key step an acid catalyzed 6-endo ring closure of b-hydroperoxy trans-epoxides directed by a vinyl group adjacent to the epoxide function. By this route, an advanced intermediate of plakortolides was obtained in six steps and 35% overall yield. The second approach featured a 1,2-dioxane ring forming by a double opening of bis-epoxides by ethereal hydrogen peroxide. This reaction did not proceed in the expected sense and exclusive formation of hydroperoxy tetrahydropyran derivatives was observed via a tandem oxacyclizationehydroperoxidation sequence.
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Tetrahedron Letters, 1996
... 1994, 35, 46854688 ; (b) Shing, TKM ; Tai, VWF ; Tsui, HCJ Chem. Soc. ... Chem. Int. Ed. Engl... more ... 1994, 35, 46854688 ; (b) Shing, TKM ; Tai, VWF ; Tsui, HCJ Chem. Soc. ... Chem. Int. Ed. Engl. 1980, 19, 557 558. 9. (a) Cha, JK ; Christ, WJ ; Kishi, Y. Tetrahedron 1984, 40, 22472255 ; (b) Oishi, T. ; Iida; KY ; Hirama, M. Tetrahedron Lett. 1993, 34, 35733576. 10. ...
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ChemInform, 2000
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ChemInform, 1999
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Biochimica et Biophysica Acta (BBA) - Lipids and Lipid Metabolism, 1998
Trans polyunsaturated fatty acids are formed during processing of vegetable oils such as deodoriz... more Trans polyunsaturated fatty acids are formed during processing of vegetable oils such as deodorization and frying.The oxidative metabolism of linoleic and α-linolenic acids and of their mono-trans isomers (9cis,12trans-18:2, 9trans,12cis-18:2 and 9cis,12cis,15trans-18:3, 9trans,12cis,15cis-18:3, respectively) was studied in fasting rats. A single dose of 18.5MBq of each [1-14C] labelled fatty acid (260μg) was orally given to the animals. The 14CO2 expired
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Tetrahedron Letters, 1999
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Tetrahedron, 1996
γ-butyrolactones are obtained in good yields from 4-trimethylsilyl-3-alkyn-1-ols via Wacker-type ... more γ-butyrolactones are obtained in good yields from 4-trimethylsilyl-3-alkyn-1-ols via Wacker-type oxidation reaction. A mechanism is proposed for this transformation: it involves two successive trans-hydroxypalladations followed by a [PdXSiMe3] syn-elimination and explains why the presence of the silyl group is essential in such a process.
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ChemInform, 1999
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ChemInform, 2000
ABSTRACT ChemInform is a weekly Abstracting Service, delivering concise information at a glance t... more ABSTRACT ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.
Bookmarks Related papers MentionsView impact
ChemInform, 1999
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Tetrahedron Letters, 1996
... All fights reserved 00404039 96 15.00 + 0.00 Total Synthesis of (+)Goniodiol JeanPhilippe Sur... more ... All fights reserved 00404039 96 15.00 + 0.00 Total Synthesis of (+)Goniodiol JeanPhilippe Surivet,Jacques Gor and JeanMichel Vatle* Laboratoire de Chimie Organique 1, associ au CNRS, Universit ... 15. Ley, SV ; Norman, J. ; Griffith, WP ; Marsden, SP Synthesis 1994, 639666. ...
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Tetrahedron: Asymmetry, 1996
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Tetrahedron: Asymmetry, 1998
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Tetrahedron Letters, 1997
Synthesis of enantiopure (+)-7-epi-goniofufurone, 1 and (+)-goniopypyrone 2 has been achieved fro... more Synthesis of enantiopure (+)-7-epi-goniofufurone, 1 and (+)-goniopypyrone 2 has been achieved from C-4 carbon chain chiron 3, readily available from (R)-mandelic acid.
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Tetrahedron Letters, 1998
(+)-Goniodiol 7 and (+)-9-deoxygoniopypyrone 8, belonging to the group of styryllactones, have be... more (+)-Goniodiol 7 and (+)-9-deoxygoniopypyrone 8, belonging to the group of styryllactones, have been synthesized in five steps and 75% yield respectively from C4-esters 1a and 1b. The key step of these syntheses is a triflate-sulfone coupling which allowed a rapid construction of the backbone of the title compounds as well as the efficient installation of a masked Z-acrylate moiety.
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Tetrahedron Letters, 1999
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