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

doi:10.1055/s-2007-983785

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 journal › Article › peer-review

15 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 language	English
Pages (from-to)	2471-2480
Number of pages	10
Journal	Synthesis
Issue number	16
DOIs	https://doi.org/10.1055/s-2007-983785
Publication status	Published - Aug 16 2007
Externally published	Yes

Keywords

Amino acids
Natural products
Tabtoxinine-β-lactam
Total synthesis
β-lactam

ASJC Scopus subject areas

Catalysis
Organic Chemistry

Access to Document

10.1055/s-2007-983785

Cite this

@article{4bdfa526b8104f6685d74d572b7c224d,

title = "Synthesis of (-)-tabtoxinine-β-lactam, the phytotoxin of tobacco wildfire disease",

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.",

keywords = "Amino acids, Natural products, Tabtoxinine-β-lactam, Total synthesis, β-lactam",

author = "Hiromasa Kiyota and Takafumi Takai and Yasuharu Shimasaki and Masatoshi Saitoh and Osamu Nakayama and Tomoko Takada and Shigefumi Kuwahara",

year = "2007",

month = aug,

day = "16",

doi = "10.1055/s-2007-983785",

language = "English",

pages = "2471--2480",

journal = "Synthesis",

issn = "0039-7881",

publisher = "Georg Thieme Verlag",

number = "16",

}

TY - JOUR

T1 - Synthesis of (-)-tabtoxinine-β-lactam, the phytotoxin of tobacco wildfire disease

AU - Kiyota, Hiromasa

AU - Takai, Takafumi

AU - Shimasaki, Yasuharu

AU - Saitoh, Masatoshi

AU - Nakayama, Osamu

AU - Takada, Tomoko

AU - Kuwahara, Shigefumi

PY - 2007/8/16

Y1 - 2007/8/16

N2 - 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.

AB - 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.

KW - Amino acids

KW - Natural products

KW - Tabtoxinine-β-lactam

KW - Total synthesis

KW - β-lactam

UR - http://www.scopus.com/inward/record.url?scp=34548319472&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=34548319472&partnerID=8YFLogxK

U2 - 10.1055/s-2007-983785

DO - 10.1055/s-2007-983785

M3 - Article

AN - SCOPUS:34548319472

SN - 0039-7881

SP - 2471

EP - 2480

JO - Synthesis

JF - Synthesis

IS - 16

ER -

Synthesis of (-)-tabtoxinine-β-lactam, the phytotoxin of tobacco wildfire disease

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this