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

20 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

Access to Document

10.1016/j.tetlet.2004.09.033

Cite this

@article{2b065209a5e04ad2a5c4e64ca8cfa8cd,

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. ",

year = "2004",

month = oct,

day = "25",

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

language = "English",

volume = "45",

pages = "8191--8194",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Limited",

number = "44",

}

TY - JOUR

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.

UR - http://www.scopus.com/inward/record.url?scp=4744344729&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=4744344729&partnerID=8YFLogxK

U2 - 10.1016/j.tetlet.2004.09.033

DO - 10.1016/j.tetlet.2004.09.033

M3 - Article

AN - SCOPUS:4744344729

VL - 45

SP - 8191

EP - 8194

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 44

ER -

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

Abstract

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this