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

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    14 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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    Keywords

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

    ASJC Scopus subject areas

    • Biochemistry
    • Organic Chemistry
    • Drug Discovery

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