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

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

Research output: Contribution to journal › Article

18 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

Fingerprint

Lactams
Tobacco
Isomers
Serine
Amides
Zinc
tabtoxinine

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

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

Facile synthesis of (-)-tabtoxinine-β-lactam and its (3′R)-isomer. / Kiyota, Hiromasa; Takai, Takafumi; Saitoh, Masatoshi; Nakayama, Osamu; Oritani, Takayuki; Kuwahara, Shigefumi.

In: Tetrahedron Letters, Vol. 45, No. 44, 25.10.2004, p. 8191-8194.

Research output: Contribution to journal › Article

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, vol. 45, no. 44, pp. 8191-8194. https://doi.org/10.1016/j.tetlet.2004.09.033
Kiyota H, Takai T, Saitoh M, Nakayama O, Oritani T, Kuwahara S. Facile synthesis of (-)-tabtoxinine-β-lactam and its (3′R)-isomer. Tetrahedron Letters. 2004 Oct 25;45(44):8191-8194. https://doi.org/10.1016/j.tetlet.2004.09.033
Kiyota, Hiromasa ; Takai, Takafumi ; Saitoh, Masatoshi ; Nakayama, Osamu ; Oritani, Takayuki ; Kuwahara, Shigefumi. / Facile synthesis of (-)-tabtoxinine-β-lactam and its (3′R)-isomer. In: Tetrahedron Letters. 2004 ; Vol. 45, No. 44. pp. 8191-8194.
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