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Rodney A Fernandes - One of the best experts on this subject based on the ideXlab platform.

  • total synthesis of the sensitive triyne natural product 4s 5s 4 8 dihydroxy 3 4 dihydrovernoniyne and all of its stereoisomers
    Organic Letters, 2019
    Co-Authors: Gujjula V Ramakrishna, Rodney A Fernandes
    Abstract:

    An efficient total synthesis of the revised structure of the sensitive triyne natural product, (4S,5S)-4,8-dihydroxy-3,4-dihydrovernoniyne, and all of its stereoisomers, that is, the previously proposed (4S,5R), (4R,5R), and (4R,5S), has been accomplished from chiral pool compounds l-mannonic-γ-lactone and d-glucono-δ-lactone. The key features involve a one-pot conversion of the chiral pool compounds into the γ-vinyl-β-hydroxy-γ-lactones, the heteroatom-directed Wacker oxidation, the Seyferth-Gilbert Reaction, and Cadiot-Chodkiewicz coupling. The synthesis also involves minimal protecting groups (only tert-butyldimethylsilyl) and is completed in seven to eight steps.

Gujjula V Ramakrishna - One of the best experts on this subject based on the ideXlab platform.

  • total synthesis of the sensitive triyne natural product 4s 5s 4 8 dihydroxy 3 4 dihydrovernoniyne and all of its stereoisomers
    Organic Letters, 2019
    Co-Authors: Gujjula V Ramakrishna, Rodney A Fernandes
    Abstract:

    An efficient total synthesis of the revised structure of the sensitive triyne natural product, (4S,5S)-4,8-dihydroxy-3,4-dihydrovernoniyne, and all of its stereoisomers, that is, the previously proposed (4S,5R), (4R,5R), and (4R,5S), has been accomplished from chiral pool compounds l-mannonic-γ-lactone and d-glucono-δ-lactone. The key features involve a one-pot conversion of the chiral pool compounds into the γ-vinyl-β-hydroxy-γ-lactones, the heteroatom-directed Wacker oxidation, the Seyferth-Gilbert Reaction, and Cadiot-Chodkiewicz coupling. The synthesis also involves minimal protecting groups (only tert-butyldimethylsilyl) and is completed in seven to eight steps.

Ra Fernandes - One of the best experts on this subject based on the ideXlab platform.

  • Total Synthesis of the Sensitive Triyne Natural Product (4S,5S)-4,8-Dihydroxy-3,4-dihydrovernoniyne and All of Its Stereoisomers
    AMER CHEMICAL SOC, 2019
    Co-Authors: Gv Ramakrishna, Ra Fernandes
    Abstract:

    An efficient total synthesis of the revised structure of the sensitive triyne natural product, (4S,5S)-4,8-dihydroxy-3,4-dihydrovernoniyne, and all of its stereoisomers, that is, the previously proposed (4S,5R), (4R,5R), and (4R,5S), has been accomplished from chiral pool compounds L-mannonic-gamma-lactone and D-glucono-delta-lactone. The key features involve a one-pot conversion of the chiral pool compounds into the gamma-vinyl-beta-hydroxy-gamma-lactones, the heteroatom-directed Wacker oxidation, the Seyferth-Gilbert Reaction, and Cadiot-Chodkiewicz coupling. The synthesis also involves minimal protecting groups (only tert-butyldimethylsilyl) and is completed in seven to eight steps

Gv Ramakrishna - One of the best experts on this subject based on the ideXlab platform.

  • Total Synthesis of the Sensitive Triyne Natural Product (4S,5S)-4,8-Dihydroxy-3,4-dihydrovernoniyne and All of Its Stereoisomers
    AMER CHEMICAL SOC, 2019
    Co-Authors: Gv Ramakrishna, Ra Fernandes
    Abstract:

    An efficient total synthesis of the revised structure of the sensitive triyne natural product, (4S,5S)-4,8-dihydroxy-3,4-dihydrovernoniyne, and all of its stereoisomers, that is, the previously proposed (4S,5R), (4R,5R), and (4R,5S), has been accomplished from chiral pool compounds L-mannonic-gamma-lactone and D-glucono-delta-lactone. The key features involve a one-pot conversion of the chiral pool compounds into the gamma-vinyl-beta-hydroxy-gamma-lactones, the heteroatom-directed Wacker oxidation, the Seyferth-Gilbert Reaction, and Cadiot-Chodkiewicz coupling. The synthesis also involves minimal protecting groups (only tert-butyldimethylsilyl) and is completed in seven to eight steps

Yasunami Masafumi - One of the best experts on this subject based on the ideXlab platform.

  • Molecular Transformation of 2-Methylazulenes: An Efficient and Practical Synthesis of 2-Formyl- and 2-Ethynylazulenes
    WILEY-V C H VERLAG GMBH, 2018
    Co-Authors: Shoji Taku, Araki Takanori, Iida Nanami, Kobayashi Yoshiaki, Ohta Akira, Sekiguchi Ryuta, Ito Shunji, Mori Shigeki, Okujima Tetsuo, Yasunami Masafumi
    Abstract:

    First published: 09 Jan 20182-Formylazulene derivatives have been obtained in good yields by the Reactions of 2-methylazulenes with N,N-dimethylformamide dimethyl acetal, followed by oxidative cleavage of the intermediately formed enamines with NaIO4. Vilsmeier formylation of 1-phenyl-3-methylazulenes also afforded the corresponding 2-formylazulenes in moderate yields. The treatment of a 2-methylazulene derivative bearing a formyl group at the 1-position with sodium methoxide led, through a self-condensation Reaction, to a trans-1-(azulen-1-yl)-2-(azulen-2-yl)ethylene derivative, the structure of which was verified by single-crystal X-ray diffraction analysis. The 2-formylazulenes obtained were transformed into 2-ethynylazulenes in good yields by a modified Seyferth-Gilbert Reaction. The reactivity of a 1-iodoazulene bearing a 2-formyl function in palladium-catalyzed cross-coupling Reactions has also been examined