Synthesis of (-)-tabtoxinine-β-lactam, the phytotoxin of tobacco wildfire disease

Hiromasa Kiyota, Takafumi Takai, Yasuharu Shimasaki, Masatoshi Saitoh, Osamu Nakayama, Tomoko Takada, Shigefumi Kuwahara

    Research output: Contribution to journalArticlepeer-review

    15 Citations (Scopus)

    Abstract

    Synthesis of (-)-tabtoxinine-β-lactam and its (3R)-isomer, the cause of tobacco wildfire disease, was achieved from L-serine using a zinc-mediated coupling reaction, Sharpless asymmetric dihydroxylation and lactamization of β-mesyloxy benzylhydroxamate amide as the key steps.

    Original languageEnglish
    Pages (from-to)2471-2480
    Number of pages10
    JournalSynthesis
    Issue number16
    DOIs
    Publication statusPublished - 2007 Aug 16

    Keywords

    • Amino acids
    • Natural products
    • Tabtoxinine-β-lactam
    • Total synthesis
    • β-lactam

    ASJC Scopus subject areas

    • Catalysis
    • Organic Chemistry

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