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

12 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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