Total Synthesis of PF1163B

Aakash Sengupta, Seijiro Hosokawa

    Research output: Contribution to journalArticle

    1 Citation (Scopus)

    Abstract

    A total synthesis of PF1163B has been achieved. The vinylogous Mukaiyama aldol reaction of ketene silyl N, O -acetal 6 (ent - 6) mediated by excess TiCl 4 proceeded with saturated aldehydes to give adduct 10 in moderate yield with moderate stereoselectivity. The major isomer is the diastereomer that was provided by using one equivalent of TiCl 4 . The Birch reduction of α,β-unsaturated imide 4, possessing a less hindered side chain, gave 12 in good stereoselectivity by employing 2-isopropylbenzimidazole as a bulky proton source. After elongation of the carbon chain and connection with the amino acid part, we accomplished a total synthesis of PF1163B. These methods constitute a concise synthetic route to obtain polyketides as well as depsipeptides.

    Original languageEnglish
    Pages (from-to)709-712
    Number of pages4
    JournalSynlett
    Volume30
    Issue number6
    DOIs
    Publication statusPublished - 2019 Jan 1

    Fingerprint

    Stereoselectivity
    Depsipeptides
    Imides
    Polyketides
    Acetals
    Aldehydes
    Isomers
    Protons
    Elongation
    Carbon
    Amino Acids
    PF 1163B
    3-hydroxybutanal
    ketene

    Keywords

    • bulky proton source
    • depsipeptide
    • PF1163B
    • stereoswitching
    • total synthesis
    • vinylogous Mukaiyama aldol reaction

    ASJC Scopus subject areas

    • Organic Chemistry

    Cite this

    Total Synthesis of PF1163B. / Sengupta, Aakash; Hosokawa, Seijiro.

    In: Synlett, Vol. 30, No. 6, 01.01.2019, p. 709-712.

    Research output: Contribution to journalArticle

    Sengupta, Aakash ; Hosokawa, Seijiro. / Total Synthesis of PF1163B. In: Synlett. 2019 ; Vol. 30, No. 6. pp. 709-712.
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