The Experts below are selected from a list of 36 Experts worldwide ranked by ideXlab platform
Enrique Mann - One of the best experts on this subject based on the ideXlab platform.
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first total synthesis of the pyrrolizidine alkaloid amphorogynine c through intramolecular azide olefin cycloaddition
European Journal of Organic Chemistry, 2012Co-Authors: Irene De Miguel, Bernardo Herradón, Marina Velado, Enrique MannAbstract:The first total synthesis of the natural alkaloid amphorogynine C is reported (2.9 % overall yield in 20 steps). The key steps include a Claisen–Johnson Rearrangement and an intramolecular azide–olefin cycloaddition, followed by a reduction of the resulting imine. The construction of the pyrrolizidine skeleton was achieved by an alkoxide-mediatedlactone ring opening and subsequent cyclization of a conveniently functionalized bicyclic amine. Finally, the proposed structure of amphorogynine C was confirmed by single-crystal X-ray diffraction analysis.
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First Total Synthesis of the Pyrrolizidine Alkaloid Amphorogynine C through Intramolecular Azide–Olefin Cycloaddition
European Journal of Organic Chemistry, 2012Co-Authors: Irene De Miguel, Bernardo Herradón, Marina Velado, Enrique MannAbstract:The first total synthesis of the natural alkaloid amphorogynine C is reported (2.9 % overall yield in 20 steps). The key steps include a Claisen–Johnson Rearrangement and an intramolecular azide–olefin cycloaddition, followed by a reduction of the resulting imine. The construction of the pyrrolizidine skeleton was achieved by an alkoxide-mediatedlactone ring opening and subsequent cyclization of a conveniently functionalized bicyclic amine. Finally, the proposed structure of amphorogynine C was confirmed by single-crystal X-ray diffraction analysis.
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Preparation of Sugar Amino Acids by Claisen-Johnson Rearrangement: Synthesis and Incorporation into Enkephalin Analogues
European Journal of Organic Chemistry, 2004Co-Authors: Ana Montero, Enrique Mann, Bernardo HerradónAbstract:We have developed a convenient route for the synthesis of an unsaturated branched sugar bearing a carboxylic acid and an amino group (masked as an azide group) by employing a totally stereoselective Claisen−Johnson Rearrangement as the key step. Several Met- and Leu-enkephalin analogues with different substitution patterns at the N- and C-termini were prepared by incorporating this sugar amino acid (SAA) as a substitute for the central Gly−Gly fragment of the parent pentapeptides. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)
Bernardo Herradón - One of the best experts on this subject based on the ideXlab platform.
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first total synthesis of the pyrrolizidine alkaloid amphorogynine c through intramolecular azide olefin cycloaddition
European Journal of Organic Chemistry, 2012Co-Authors: Irene De Miguel, Bernardo Herradón, Marina Velado, Enrique MannAbstract:The first total synthesis of the natural alkaloid amphorogynine C is reported (2.9 % overall yield in 20 steps). The key steps include a Claisen–Johnson Rearrangement and an intramolecular azide–olefin cycloaddition, followed by a reduction of the resulting imine. The construction of the pyrrolizidine skeleton was achieved by an alkoxide-mediatedlactone ring opening and subsequent cyclization of a conveniently functionalized bicyclic amine. Finally, the proposed structure of amphorogynine C was confirmed by single-crystal X-ray diffraction analysis.
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First Total Synthesis of the Pyrrolizidine Alkaloid Amphorogynine C through Intramolecular Azide–Olefin Cycloaddition
European Journal of Organic Chemistry, 2012Co-Authors: Irene De Miguel, Bernardo Herradón, Marina Velado, Enrique MannAbstract:The first total synthesis of the natural alkaloid amphorogynine C is reported (2.9 % overall yield in 20 steps). The key steps include a Claisen–Johnson Rearrangement and an intramolecular azide–olefin cycloaddition, followed by a reduction of the resulting imine. The construction of the pyrrolizidine skeleton was achieved by an alkoxide-mediatedlactone ring opening and subsequent cyclization of a conveniently functionalized bicyclic amine. Finally, the proposed structure of amphorogynine C was confirmed by single-crystal X-ray diffraction analysis.
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Preparation of Sugar Amino Acids by Claisen-Johnson Rearrangement: Synthesis and Incorporation into Enkephalin Analogues
European Journal of Organic Chemistry, 2004Co-Authors: Ana Montero, Enrique Mann, Bernardo HerradónAbstract:We have developed a convenient route for the synthesis of an unsaturated branched sugar bearing a carboxylic acid and an amino group (masked as an azide group) by employing a totally stereoselective Claisen−Johnson Rearrangement as the key step. Several Met- and Leu-enkephalin analogues with different substitution patterns at the N- and C-termini were prepared by incorporating this sugar amino acid (SAA) as a substitute for the central Gly−Gly fragment of the parent pentapeptides. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)
Irene De Miguel - One of the best experts on this subject based on the ideXlab platform.
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first total synthesis of the pyrrolizidine alkaloid amphorogynine c through intramolecular azide olefin cycloaddition
European Journal of Organic Chemistry, 2012Co-Authors: Irene De Miguel, Bernardo Herradón, Marina Velado, Enrique MannAbstract:The first total synthesis of the natural alkaloid amphorogynine C is reported (2.9 % overall yield in 20 steps). The key steps include a Claisen–Johnson Rearrangement and an intramolecular azide–olefin cycloaddition, followed by a reduction of the resulting imine. The construction of the pyrrolizidine skeleton was achieved by an alkoxide-mediatedlactone ring opening and subsequent cyclization of a conveniently functionalized bicyclic amine. Finally, the proposed structure of amphorogynine C was confirmed by single-crystal X-ray diffraction analysis.
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First Total Synthesis of the Pyrrolizidine Alkaloid Amphorogynine C through Intramolecular Azide–Olefin Cycloaddition
European Journal of Organic Chemistry, 2012Co-Authors: Irene De Miguel, Bernardo Herradón, Marina Velado, Enrique MannAbstract:The first total synthesis of the natural alkaloid amphorogynine C is reported (2.9 % overall yield in 20 steps). The key steps include a Claisen–Johnson Rearrangement and an intramolecular azide–olefin cycloaddition, followed by a reduction of the resulting imine. The construction of the pyrrolizidine skeleton was achieved by an alkoxide-mediatedlactone ring opening and subsequent cyclization of a conveniently functionalized bicyclic amine. Finally, the proposed structure of amphorogynine C was confirmed by single-crystal X-ray diffraction analysis.
Marina Velado - One of the best experts on this subject based on the ideXlab platform.
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first total synthesis of the pyrrolizidine alkaloid amphorogynine c through intramolecular azide olefin cycloaddition
European Journal of Organic Chemistry, 2012Co-Authors: Irene De Miguel, Bernardo Herradón, Marina Velado, Enrique MannAbstract:The first total synthesis of the natural alkaloid amphorogynine C is reported (2.9 % overall yield in 20 steps). The key steps include a Claisen–Johnson Rearrangement and an intramolecular azide–olefin cycloaddition, followed by a reduction of the resulting imine. The construction of the pyrrolizidine skeleton was achieved by an alkoxide-mediatedlactone ring opening and subsequent cyclization of a conveniently functionalized bicyclic amine. Finally, the proposed structure of amphorogynine C was confirmed by single-crystal X-ray diffraction analysis.
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First Total Synthesis of the Pyrrolizidine Alkaloid Amphorogynine C through Intramolecular Azide–Olefin Cycloaddition
European Journal of Organic Chemistry, 2012Co-Authors: Irene De Miguel, Bernardo Herradón, Marina Velado, Enrique MannAbstract:The first total synthesis of the natural alkaloid amphorogynine C is reported (2.9 % overall yield in 20 steps). The key steps include a Claisen–Johnson Rearrangement and an intramolecular azide–olefin cycloaddition, followed by a reduction of the resulting imine. The construction of the pyrrolizidine skeleton was achieved by an alkoxide-mediatedlactone ring opening and subsequent cyclization of a conveniently functionalized bicyclic amine. Finally, the proposed structure of amphorogynine C was confirmed by single-crystal X-ray diffraction analysis.
E P Serebryakov - One of the best experts on this subject based on the ideXlab platform.
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access to 2 4 dien 6 ynoic acid esters using selenium chemistry formal synthesis of z z dodeca 3 6 dien 1 ol trail pheromone mimic of the subterranian termite reticulitermes virginicus and z z dodeca 3 6 dien 11 olide aggregation pheromone of the gra
Journal of Chemical Research-s, 1998Co-Authors: Andrei A Vasilev, Lars Engman, E P SerebryakovAbstract:Esters of 2,4-dien-6-ynoic acids were prepared from terminal acetylenes by lithiation, 1,2-addition to acrolein, orthoester Claisen–Johnson Rearrangement and α-(4-methoxyphenyl)selenation/oxidative elimination to introduce the α,β-unsaturation.
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Access to 2,4-dien-6-ynoic acid esters using selenium chemistry. Formal synthesis of Z,Z-dodeca-3,6-dien-1-ol (trail pheromone mimic of the subterranian termite Reticulitermes virginicus) and Z,Z-dodeca-3,6-dien-11-olide (aggregation pheromone of the
Journal of Chemical Research-s, 1998Co-Authors: Andrei A. Vasil'ev, Lars Engman, E P SerebryakovAbstract:Esters of 2,4-dien-6-ynoic acids were prepared from terminal acetylenes by lithiation, 1,2-addition to acrolein, orthoester Claisen-Johnson Rearrangement and alpha-(4-methoxyphenyl)selenation/oxidative elimination to introduce the alpha,beta-unsaturation