A short and enantioselective preparation of taxol A-ring fragment

Sho Hirai, Naoko Urushizako, Masayuki Miyano, Tomohiro Fujii, Masahisa Nakada

    Research output: Contribution to journalArticle

    5 Citations (Scopus)

    Abstract

    Two short preparations of the taxol A-ring fragment are described: one via organocatalyzed α-aminoxylation and the other via Sharpless asymmetric dihydroxylation (SAD). The former approach affords the A-ring fragment in 10 steps, and the latter approach involves eight steps to afford the new A-ring fragment in 91% ee, which is made enantiomerically pure through recrystallization. The new A-ring fragment bearing a bromoalkene is confirmed to be useful to form the carbocyclic eight-membered ring of a taxol model compound by palladium-catalyzed intramolecular alkenylation. The preparation of the new A-ring fragment will be beneficial for the total synthesis of taxol as well as other natural products.

    Original languageEnglish
    Pages (from-to)1888-1892
    Number of pages5
    JournalTetrahedron Letters
    Volume54
    Issue number14
    DOIs
    Publication statusPublished - 2013 Apr 3

    Fingerprint

    Paclitaxel
    Alkenylation
    Bearings (structural)
    Palladium
    Biological Products

    Keywords

    • Dihydroxylation
    • Enantioselective
    • Organocatalysis
    • Stereoselective
    • Taxol

    ASJC Scopus subject areas

    • Biochemistry
    • Organic Chemistry
    • Drug Discovery

    Cite this

    A short and enantioselective preparation of taxol A-ring fragment. / Hirai, Sho; Urushizako, Naoko; Miyano, Masayuki; Fujii, Tomohiro; Nakada, Masahisa.

    In: Tetrahedron Letters, Vol. 54, No. 14, 03.04.2013, p. 1888-1892.

    Research output: Contribution to journalArticle

    Hirai, Sho ; Urushizako, Naoko ; Miyano, Masayuki ; Fujii, Tomohiro ; Nakada, Masahisa. / A short and enantioselective preparation of taxol A-ring fragment. In: Tetrahedron Letters. 2013 ; Vol. 54, No. 14. pp. 1888-1892.
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    AU - Nakada, Masahisa

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