Synthetic studies on (-)-FR182877: construction of the ABCD ring system via the intramolecular cycloadditions (1)

Takahiro Suzuki, Natsumi Tanaka, Takehiko Matsumura, Yosuke Hosoya, Masahisa Nakada

    Research output: Contribution to journalArticle

    10 Citations (Scopus)

    Abstract

    Construction of the ABCD ring system of (-)-FR182877 via the highly diastereoselective intramolecular Diels-Alder (IMDA) reaction is described. The IMDA reaction of the α,β-unsaturated aldehyde generated in situ from the corresponding acetal successfully provided the desired product 14 possessing the AB ring system as the single diastereomer. The CD ring system was constructed by the subsequent IMHDA reaction and the additional experiment suggested that the diastereoselectivity of the IMHDA reaction could be related to the E/Z geometry of alkene 17, which was generated in situ from 16.

    Original languageEnglish
    Pages (from-to)6483-6487
    Number of pages5
    JournalTetrahedron Letters
    Volume48
    Issue number37
    DOIs
    Publication statusPublished - 2007 Sep 10

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    Acetals
    Cycloaddition
    Cycloaddition Reaction
    Alkenes
    Aldehydes
    Geometry
    Experiments
    FR 182877

    ASJC Scopus subject areas

    • Biochemistry
    • Organic Chemistry
    • Drug Discovery

    Cite this

    Synthetic studies on (-)-FR182877 : construction of the ABCD ring system via the intramolecular cycloadditions (1). / Suzuki, Takahiro; Tanaka, Natsumi; Matsumura, Takehiko; Hosoya, Yosuke; Nakada, Masahisa.

    In: Tetrahedron Letters, Vol. 48, No. 37, 10.09.2007, p. 6483-6487.

    Research output: Contribution to journalArticle

    Suzuki, Takahiro ; Tanaka, Natsumi ; Matsumura, Takehiko ; Hosoya, Yosuke ; Nakada, Masahisa. / Synthetic studies on (-)-FR182877 : construction of the ABCD ring system via the intramolecular cycloadditions (1). In: Tetrahedron Letters. 2007 ; Vol. 48, No. 37. pp. 6483-6487.
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    AU - Nakada, Masahisa

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