Facile synthesis of (-)-tabtoxinine-β-lactam and its (3′R)-isomer

Hiromasa Kiyota, Takafumi Takai, Masatoshi Saitoh, Osamu Nakayama, Takayuki Oritani, Shigefumi Kuwahara

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19 Citations (Scopus)

Abstract

A concise and high yielding synthesis of (-)-tabtoxinine-β-lactam 1, the cause of tobacco wildfire disease, was achieved from l-serine. A concise and high yielding synthesis of (-)-tabtoxinine-β-lactam 1, the cause of tobacco wildfire disease, was achieved from l-serine using a zinc-mediated coupling reaction, Sharpless asymmetric dihydroxylation and lactamization of N-OBn amide as the key steps.

Original languageEnglish
Pages (from-to)8191-8194
Number of pages4
JournalTetrahedron Letters
Volume45
Issue number44
DOIs
Publication statusPublished - Oct 25 2004
Externally publishedYes

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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  • Cite this

    Kiyota, H., Takai, T., Saitoh, M., Nakayama, O., Oritani, T., & Kuwahara, S. (2004). Facile synthesis of (-)-tabtoxinine-β-lactam and its (3′R)-isomer. Tetrahedron Letters, 45(44), 8191-8194. https://doi.org/10.1016/j.tetlet.2004.09.033