Total Synthesis of PF1163B

Aakash Sengupta, Seijiro Hosokawa

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    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

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    Keywords

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

    ASJC Scopus subject areas

    • Organic Chemistry

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