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

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

doi:10.1016/j.tetlet.2004.09.033

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 › peer-review

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 language	English
Pages (from-to)	8191-8194
Number of pages	4
Journal	Tetrahedron Letters
Volume	45
Issue number	44
DOIs	https://doi.org/10.1016/j.tetlet.2004.09.033
Publication status	Published - Oct 25 2004
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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title = "Facile synthesis of (-)-tabtoxinine-β-lactam and its (3′R)-isomer",

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.",

author = "Hiromasa Kiyota and Takafumi Takai and Masatoshi Saitoh and Osamu Nakayama and Takayuki Oritani and Shigefumi Kuwahara",

note = "Funding Information: We thank Dr. Yoshifumi Itoh [Akita Research Institute of Food and Brewing (ARIF)] for academic assistance. This work was partially supported by a Grant-in-aid for Scientific Research from Japan Society for the Promotion of Science (No. 14760069), The Agricultural Chemical Research Foundation, Intelligent Cosmos Foundation and The Naito Foundation. ",

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doi = "10.1016/j.tetlet.2004.09.033",

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T1 - Facile synthesis of (-)-tabtoxinine-β-lactam and its (3′R)-isomer

AU - Kiyota, Hiromasa

AU - Takai, Takafumi

AU - Saitoh, Masatoshi

AU - Nakayama, Osamu

AU - Oritani, Takayuki

AU - Kuwahara, Shigefumi

N1 - Funding Information: We thank Dr. Yoshifumi Itoh [Akita Research Institute of Food and Brewing (ARIF)] for academic assistance. This work was partially supported by a Grant-in-aid for Scientific Research from Japan Society for the Promotion of Science (No. 14760069), The Agricultural Chemical Research Foundation, Intelligent Cosmos Foundation and The Naito Foundation.

PY - 2004/10/25

Y1 - 2004/10/25

N2 - 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.

AB - 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.

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