Development of silicon-tethered anionic reaction and its application to the synthesis of chiral A-ring moieties of Taxol™

Mitsuhiro Iwamoto, Masayuki Miyano, Masayuki Utsugi, Hatsuo Kawada, Masahisa Nakada

    Research output: Contribution to journalArticle

    13 Citations (Scopus)

    Abstract

    Silicon-tethered intramolecular nucleophilic additions of a hydroxymethyl unit to ketones in β-hydroxyketones have been developed. The product obtained by this protocol was successfully converted to chiral A-ring moieties of Taxol™. Also developed was a promising silicon-tethered intramolecular α-alkylation reaction of the cyclic hydroxyketone.

    Original languageEnglish
    Pages (from-to)8647-8651
    Number of pages5
    JournalTetrahedron Letters
    Volume45
    Issue number47
    DOIs
    Publication statusPublished - 2004 Nov 15

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    Silicon
    Paclitaxel
    Alkylation
    Ketones

    Keywords

    • Alkylation
    • Carbanion
    • Intramolecular reaction
    • Nucleophilic addition
    • Silicon tethered
    • Taxol™

    ASJC Scopus subject areas

    • Biochemistry
    • Organic Chemistry
    • Drug Discovery

    Cite this

    Development of silicon-tethered anionic reaction and its application to the synthesis of chiral A-ring moieties of Taxol™. / Iwamoto, Mitsuhiro; Miyano, Masayuki; Utsugi, Masayuki; Kawada, Hatsuo; Nakada, Masahisa.

    In: Tetrahedron Letters, Vol. 45, No. 47, 15.11.2004, p. 8647-8651.

    Research output: Contribution to journalArticle

    Iwamoto, Mitsuhiro ; Miyano, Masayuki ; Utsugi, Masayuki ; Kawada, Hatsuo ; Nakada, Masahisa. / Development of silicon-tethered anionic reaction and its application to the synthesis of chiral A-ring moieties of Taxol™. In: Tetrahedron Letters. 2004 ; Vol. 45, No. 47. pp. 8647-8651.
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    AU - Kawada, Hatsuo

    AU - Nakada, Masahisa

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