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Chung K. Chu - One of the best experts on this subject based on the ideXlab platform.

  • Stereocontrolled syntheses of Carbocyclic C-nucleosides and related Compounds.
    The Journal of organic chemistry, 2001
    Co-Authors: Byoung K. Chun, Gyu Y. Song, Chung K. Chu
    Abstract:

    Carbocyclic 9-deazapurine nucleosides (1−4), a spiranic pyrimidone Carbocyclic Compound (5), and an unusual Carbocyclic isonucleoside (6) were prepared as enantiomerically pure Compounds via the key intermediates 10 and 21 from 1,4-γ-ribonolactone. The key intermediate 10 was prepared by stereoselective reduction with Bu3SnH and then converted to Carbocyclic C-ribonucleosides 1, 3, and 4. 2‘,3‘-Didehydro-2‘,3‘-dideoxyCarbocyclic 9-deazainosine (2) was prepared from a 2‘,3‘-dimesylate 17 by treatment with Li2Te followed by an acidic deprotection. The key bicyclic intermediate 21 was prepared from a diol 20 by an intramolecular cyclization using CHI3−Ph3P−imidazole and converted to the spiranic Compound 5 and an olefinic nucleoside 6 by the construction of the heterocyclic moiety followed by deprotection.

Juan B. Rodriguez - One of the best experts on this subject based on the ideXlab platform.

Dennis G. Peters - One of the best experts on this subject based on the ideXlab platform.

Byoung K. Chun - One of the best experts on this subject based on the ideXlab platform.

  • Stereocontrolled syntheses of Carbocyclic C-nucleosides and related Compounds.
    The Journal of organic chemistry, 2001
    Co-Authors: Byoung K. Chun, Gyu Y. Song, Chung K. Chu
    Abstract:

    Carbocyclic 9-deazapurine nucleosides (1−4), a spiranic pyrimidone Carbocyclic Compound (5), and an unusual Carbocyclic isonucleoside (6) were prepared as enantiomerically pure Compounds via the key intermediates 10 and 21 from 1,4-γ-ribonolactone. The key intermediate 10 was prepared by stereoselective reduction with Bu3SnH and then converted to Carbocyclic C-ribonucleosides 1, 3, and 4. 2‘,3‘-Didehydro-2‘,3‘-dideoxyCarbocyclic 9-deazainosine (2) was prepared from a 2‘,3‘-dimesylate 17 by treatment with Li2Te followed by an acidic deprotection. The key bicyclic intermediate 21 was prepared from a diol 20 by an intramolecular cyclization using CHI3−Ph3P−imidazole and converted to the spiranic Compound 5 and an olefinic nucleoside 6 by the construction of the heterocyclic moiety followed by deprotection.

Eleonora Elhalem - One of the best experts on this subject based on the ideXlab platform.