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

18 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

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10.1055/s-2007-983785

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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",

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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 - https://www.scopus.com/pages/publications/34548319472

UR - https://www.scopus.com/pages/publications/34548319472#tab=citedBy

U2 - 10.1055/s-2007-983785

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JO - Synthesis

JF - Synthesis

IS - 16

ER -

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

Abstract

Keywords

ASJC Scopus subject areas

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