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Martin Hiersemann - One of the best experts on this subject based on the ideXlab platform.

  • Catalytic asymmetric Claisen rearrangement of Gosteli-type allyl vinyl ethers: total synthesis of (-)-9,10-dihydroecklonialactone B.
    The Journal of Organic Chemistry, 2014
    Co-Authors: Julia K. Becker, Lena Butt, Valeska Von Kiedrowski, Elisabeth Mischler, Florian Quentin, Martin Hiersemann
    Abstract:

    The enantioselective synthesis of (−)-9,10-dihydroecklonialactone B is described. The catalytic asymmetric Claisen rearrangement of a Gosteli-type allyl vinyl ether was utilized to afford an acyclic α-keto ester building block endowed with functionality amenable to the preparation of the carbocyclic target molecule by suitable postrearrangement transformations: A highly diastereoselective Corey–Bakshi–Shibata Reduction of a β-chiral α-keto ester and a reductive homologation of an α-hydroxy ester. A transprotection tactic by a chemoselective intramolecular 6-exo-trig iodoetherification enabled regioselective ring-closing alkene metatheses to afford the 5- as well as the 14-membered ring, however, with mixed success in terms of E/Z selectivity.

  • Catalytic Asymmetric Claisen Rearrangement of Gosteli-Type Allyl Vinyl Ethers: Total Synthesis of (−)-9,10-Dihydroecklonialactone B
    2014
    Co-Authors: Julia Becker, Lena Butt, Valeska Von Kiedrowski, Elisabeth Mischler, Florian Quentin, Martin Hiersemann
    Abstract:

    The enantioselective synthesis of (−)-9,10-dihydroecklonialactone B is described. The catalytic asymmetric Claisen rearrangement of a Gosteli-type allyl vinyl ether was utilized to afford an acyclic α-keto ester building block endowed with functionality amenable to the preparation of the carbocyclic target molecule by suitable postrearrangement transformations: A highly diastereoselective Corey–Bakshi–Shibata Reduction of a β-chiral α-keto ester and a reductive homologation of an α-hydroxy ester. A transprotection tactic by a chemoselective intramolecular 6-exo-trig iodoetherification enabled regioselective ring-closing alkene metatheses to afford the 5- as well as the 14-membered ring, however, with mixed success in terms of E/Z selectivity

Julia K. Becker - One of the best experts on this subject based on the ideXlab platform.

  • Catalytic asymmetric Claisen rearrangement of Gosteli-type allyl vinyl ethers: total synthesis of (-)-9,10-dihydroecklonialactone B.
    The Journal of Organic Chemistry, 2014
    Co-Authors: Julia K. Becker, Lena Butt, Valeska Von Kiedrowski, Elisabeth Mischler, Florian Quentin, Martin Hiersemann
    Abstract:

    The enantioselective synthesis of (−)-9,10-dihydroecklonialactone B is described. The catalytic asymmetric Claisen rearrangement of a Gosteli-type allyl vinyl ether was utilized to afford an acyclic α-keto ester building block endowed with functionality amenable to the preparation of the carbocyclic target molecule by suitable postrearrangement transformations: A highly diastereoselective Corey–Bakshi–Shibata Reduction of a β-chiral α-keto ester and a reductive homologation of an α-hydroxy ester. A transprotection tactic by a chemoselective intramolecular 6-exo-trig iodoetherification enabled regioselective ring-closing alkene metatheses to afford the 5- as well as the 14-membered ring, however, with mixed success in terms of E/Z selectivity.

Lena Butt - One of the best experts on this subject based on the ideXlab platform.

  • Catalytic asymmetric Claisen rearrangement of Gosteli-type allyl vinyl ethers: total synthesis of (-)-9,10-dihydroecklonialactone B.
    The Journal of Organic Chemistry, 2014
    Co-Authors: Julia K. Becker, Lena Butt, Valeska Von Kiedrowski, Elisabeth Mischler, Florian Quentin, Martin Hiersemann
    Abstract:

    The enantioselective synthesis of (−)-9,10-dihydroecklonialactone B is described. The catalytic asymmetric Claisen rearrangement of a Gosteli-type allyl vinyl ether was utilized to afford an acyclic α-keto ester building block endowed with functionality amenable to the preparation of the carbocyclic target molecule by suitable postrearrangement transformations: A highly diastereoselective Corey–Bakshi–Shibata Reduction of a β-chiral α-keto ester and a reductive homologation of an α-hydroxy ester. A transprotection tactic by a chemoselective intramolecular 6-exo-trig iodoetherification enabled regioselective ring-closing alkene metatheses to afford the 5- as well as the 14-membered ring, however, with mixed success in terms of E/Z selectivity.

  • Catalytic Asymmetric Claisen Rearrangement of Gosteli-Type Allyl Vinyl Ethers: Total Synthesis of (−)-9,10-Dihydroecklonialactone B
    2014
    Co-Authors: Julia Becker, Lena Butt, Valeska Von Kiedrowski, Elisabeth Mischler, Florian Quentin, Martin Hiersemann
    Abstract:

    The enantioselective synthesis of (−)-9,10-dihydroecklonialactone B is described. The catalytic asymmetric Claisen rearrangement of a Gosteli-type allyl vinyl ether was utilized to afford an acyclic α-keto ester building block endowed with functionality amenable to the preparation of the carbocyclic target molecule by suitable postrearrangement transformations: A highly diastereoselective Corey–Bakshi–Shibata Reduction of a β-chiral α-keto ester and a reductive homologation of an α-hydroxy ester. A transprotection tactic by a chemoselective intramolecular 6-exo-trig iodoetherification enabled regioselective ring-closing alkene metatheses to afford the 5- as well as the 14-membered ring, however, with mixed success in terms of E/Z selectivity

Valeska Von Kiedrowski - One of the best experts on this subject based on the ideXlab platform.

  • Catalytic asymmetric Claisen rearrangement of Gosteli-type allyl vinyl ethers: total synthesis of (-)-9,10-dihydroecklonialactone B.
    The Journal of Organic Chemistry, 2014
    Co-Authors: Julia K. Becker, Lena Butt, Valeska Von Kiedrowski, Elisabeth Mischler, Florian Quentin, Martin Hiersemann
    Abstract:

    The enantioselective synthesis of (−)-9,10-dihydroecklonialactone B is described. The catalytic asymmetric Claisen rearrangement of a Gosteli-type allyl vinyl ether was utilized to afford an acyclic α-keto ester building block endowed with functionality amenable to the preparation of the carbocyclic target molecule by suitable postrearrangement transformations: A highly diastereoselective Corey–Bakshi–Shibata Reduction of a β-chiral α-keto ester and a reductive homologation of an α-hydroxy ester. A transprotection tactic by a chemoselective intramolecular 6-exo-trig iodoetherification enabled regioselective ring-closing alkene metatheses to afford the 5- as well as the 14-membered ring, however, with mixed success in terms of E/Z selectivity.

  • Catalytic Asymmetric Claisen Rearrangement of Gosteli-Type Allyl Vinyl Ethers: Total Synthesis of (−)-9,10-Dihydroecklonialactone B
    2014
    Co-Authors: Julia Becker, Lena Butt, Valeska Von Kiedrowski, Elisabeth Mischler, Florian Quentin, Martin Hiersemann
    Abstract:

    The enantioselective synthesis of (−)-9,10-dihydroecklonialactone B is described. The catalytic asymmetric Claisen rearrangement of a Gosteli-type allyl vinyl ether was utilized to afford an acyclic α-keto ester building block endowed with functionality amenable to the preparation of the carbocyclic target molecule by suitable postrearrangement transformations: A highly diastereoselective Corey–Bakshi–Shibata Reduction of a β-chiral α-keto ester and a reductive homologation of an α-hydroxy ester. A transprotection tactic by a chemoselective intramolecular 6-exo-trig iodoetherification enabled regioselective ring-closing alkene metatheses to afford the 5- as well as the 14-membered ring, however, with mixed success in terms of E/Z selectivity

Elisabeth Mischler - One of the best experts on this subject based on the ideXlab platform.

  • Catalytic asymmetric Claisen rearrangement of Gosteli-type allyl vinyl ethers: total synthesis of (-)-9,10-dihydroecklonialactone B.
    The Journal of Organic Chemistry, 2014
    Co-Authors: Julia K. Becker, Lena Butt, Valeska Von Kiedrowski, Elisabeth Mischler, Florian Quentin, Martin Hiersemann
    Abstract:

    The enantioselective synthesis of (−)-9,10-dihydroecklonialactone B is described. The catalytic asymmetric Claisen rearrangement of a Gosteli-type allyl vinyl ether was utilized to afford an acyclic α-keto ester building block endowed with functionality amenable to the preparation of the carbocyclic target molecule by suitable postrearrangement transformations: A highly diastereoselective Corey–Bakshi–Shibata Reduction of a β-chiral α-keto ester and a reductive homologation of an α-hydroxy ester. A transprotection tactic by a chemoselective intramolecular 6-exo-trig iodoetherification enabled regioselective ring-closing alkene metatheses to afford the 5- as well as the 14-membered ring, however, with mixed success in terms of E/Z selectivity.

  • Catalytic Asymmetric Claisen Rearrangement of Gosteli-Type Allyl Vinyl Ethers: Total Synthesis of (−)-9,10-Dihydroecklonialactone B
    2014
    Co-Authors: Julia Becker, Lena Butt, Valeska Von Kiedrowski, Elisabeth Mischler, Florian Quentin, Martin Hiersemann
    Abstract:

    The enantioselective synthesis of (−)-9,10-dihydroecklonialactone B is described. The catalytic asymmetric Claisen rearrangement of a Gosteli-type allyl vinyl ether was utilized to afford an acyclic α-keto ester building block endowed with functionality amenable to the preparation of the carbocyclic target molecule by suitable postrearrangement transformations: A highly diastereoselective Corey–Bakshi–Shibata Reduction of a β-chiral α-keto ester and a reductive homologation of an α-hydroxy ester. A transprotection tactic by a chemoselective intramolecular 6-exo-trig iodoetherification enabled regioselective ring-closing alkene metatheses to afford the 5- as well as the 14-membered ring, however, with mixed success in terms of E/Z selectivity