Synthesis of C3-C21 Segment of Aflastatin A Using Remote Asymmetric Induction Reactions

Sawato Murakoshi, Seijiro Hosokawa

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    Abstract

    The C3-C21 segment of aflastatin A has been synthesized by converging three segments including the C3-C8 segment, the C9-C15 segment, and the C16-C21 segment. Each segment has been synthesized from a vinylketene silyl N,O-acetal possessing a chiral auxiliary by a wide-range stereocontrol strategy. The C3-C8 segment was constructed in seven steps including the stereoselective vinylogous Mukaiyama alkylation, while the C9-C15 segment and the C16-C21 segment were synthesized using the vinylogous Mukaiyama aldol reaction in seven and eight steps, respectively.

    Original languageEnglish
    JournalOrganic Letters
    DOIs
    Publication statusAccepted/In press - 2019 Jan 1

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    ASJC Scopus subject areas

    • Biochemistry
    • Physical and Theoretical Chemistry
    • Organic Chemistry

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