Synthetic studies on aculeximycin: Synthesis of C24-C40 segment by kobayashi aldolization and epoxide rearrangements

Takuya Kato, Tomohiko Sato, Yuki Kashiwagi, Seijiro Hosokawa*

*この研究の対応する著者

    研究成果査読

    10 被引用数 (Scopus)

    抄録

    Stereoselective synthesis of the C24-C40 segment of aculeximycin has been achieved by using the Kobayashi aldol reactions and epoxy-opening rearrangement reactions. The C33-C40 segment was synthesized by the Kobayashi aldol reaction followed by epoxidation and Jung rearrangement of epoxide 9, while the C25-C32 segment was constructed by the Kobayashi aldol reaction followed by epoxidation and the epoxy-opening rearrangement reaction of epoxide 13. These segments were connected by the aldol reaction and the sequential dehydration, reduction, and conversion of ethyl ester to ethyl ketone to give the C24-C40 segment 1. All stereogenic centers were constructed by substrate-controlled stereoselective reactions.

    本文言語English
    ページ(範囲)2274-2277
    ページ数4
    ジャーナルOrganic Letters
    17
    9
    DOI
    出版ステータスPublished - 2015 5 1

    ASJC Scopus subject areas

    • 有機化学
    • 物理化学および理論化学
    • 生化学

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