Synthetic studies on aculeximycin

Synthesis of C24-C40 segment by kobayashi aldolization and epoxide rearrangements

Takuya Kato, Tomohiko Sato, Yuki Kashiwagi, Seijiro Hosokawa

    Research output: Contribution to journalArticle

    9 Citations (Scopus)

    Abstract

    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.

    Original languageEnglish
    Pages (from-to)2274-2277
    Number of pages4
    JournalOrganic Letters
    Volume17
    Issue number9
    DOIs
    Publication statusPublished - 2015 May 1

    Fingerprint

    epoxy compounds
    Epoxy Compounds
    Epoxidation
    synthesis
    epoxidation
    Ketones
    Dehydration
    Esters
    aculeximycin
    3-hydroxybutanal
    ketones
    dehydration
    Substrates
    esters

    ASJC Scopus subject areas

    • Organic Chemistry
    • Physical and Theoretical Chemistry
    • Biochemistry

    Cite this

    Synthetic studies on aculeximycin : Synthesis of C24-C40 segment by kobayashi aldolization and epoxide rearrangements. / Kato, Takuya; Sato, Tomohiko; Kashiwagi, Yuki; Hosokawa, Seijiro.

    In: Organic Letters, Vol. 17, No. 9, 01.05.2015, p. 2274-2277.

    Research output: Contribution to journalArticle

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    AU - Hosokawa, Seijiro

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