Synthesis of (S)-ktedonoketone

Sayaka Ishii, Katsuya Saito, Shigefumi Kuwahara, Masaru Enomoto

    Research output: Contribution to journalArticlepeer-review

    2 Citations (Scopus)

    Abstract

    The first total synthesis of (S)-ktedonoketone has been accomplished in 16% overall yield from (R)-2-hydroxybutyric acid by an eight-step sequence that features a highly diastereoselective methallylation of a chiral dioxolanone and a nucleophilic addition of α-lithiostyrene to a Weinreb's amide intermediate followed by ring-closing metathesis of the resulting enone to construct an α,β-disubstituted cyclopentenone ring system. The sign of specific rotation of synthetic (S)-ktedonoketone was opposite to that reported for the natural product.

    Original languageEnglish
    Article number151915
    JournalTetrahedron Letters
    Volume61
    Issue number22
    DOIs
    Publication statusPublished - 2020 May 28

    Keywords

    • Asymmetric methallylation
    • Ktedonobacteria
    • Ktedonoketone
    • Ring-closing metathesis

    ASJC Scopus subject areas

    • Biochemistry
    • Drug Discovery
    • Organic Chemistry

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