Asymmetric total synthesis of neoxaline

Tetsuya Ideguchi; Takeshi Yamada; Tatsuya Shirahata; Tomoyasu Hirose; Akihiro Sugawara; Yoshinori Kobayashi; Satoshi Omura; Toshiaki Sunazuka

doi:10.1021/ja406657v

Asymmetric total synthesis of neoxaline

Tetsuya Ideguchi, Takeshi Yamada, Tatsuya Shirahata, Tomoyasu Hirose, Akihiro Sugawara, Yoshinori Kobayashi, Satoshi Omura, Toshiaki Sunazuka

研究成果: Article › 査読

28 被引用数 (Scopus)

抄録

A first asymmetric total synthesis and determination of the absolute configuration of neoxaline has been accomplished through the highly stereoselective introduction of a reverse prenyl group to create a quaternary carbon stereocenter using (-)-3a-hydroxyfuroindoline as a building block, construction of the indoline spiroaminal via cautious stepwise oxidations with cyclizations from the indoline, assembly of (Z)-dehydrohistidine, and photoisomerization of unnatural (Z)-neoxaline to the natural (E)-neoxaline as the key steps.

本文言語	English
ページ（範囲）	12568-12571
ページ数	4
ジャーナル	Journal of the American Chemical Society
巻	135
号	34
DOI	https://doi.org/10.1021/ja406657v
出版ステータス	Published - 2013 8 28
外部発表	はい

ASJC Scopus subject areas

Catalysis
Chemistry(all)
Biochemistry
Colloid and Surface Chemistry

文献へのアクセス

10.1021/ja406657v

フィンガープリント「Asymmetric total synthesis of neoxaline」の研究トピックを掘り下げます。これらがまとまってユニークなフィンガープリントを構成します。

引用スタイル

@article{9b3a7441df754382a83f74243325eecb,

title = "Asymmetric total synthesis of neoxaline",

abstract = "A first asymmetric total synthesis and determination of the absolute configuration of neoxaline has been accomplished through the highly stereoselective introduction of a reverse prenyl group to create a quaternary carbon stereocenter using (-)-3a-hydroxyfuroindoline as a building block, construction of the indoline spiroaminal via cautious stepwise oxidations with cyclizations from the indoline, assembly of (Z)-dehydrohistidine, and photoisomerization of unnatural (Z)-neoxaline to the natural (E)-neoxaline as the key steps.",

author = "Tetsuya Ideguchi and Takeshi Yamada and Tatsuya Shirahata and Tomoyasu Hirose and Akihiro Sugawara and Yoshinori Kobayashi and Satoshi Omura and Toshiaki Sunazuka",

year = "2013",

month = aug,

day = "28",

doi = "10.1021/ja406657v",

language = "English",

volume = "135",

pages = "12568--12571",

journal = "Journal of the American Chemical Society",

issn = "0002-7863",

publisher = "American Chemical Society",

number = "34",

}

TY - JOUR

T1 - Asymmetric total synthesis of neoxaline

AU - Ideguchi, Tetsuya

AU - Yamada, Takeshi

AU - Shirahata, Tatsuya

AU - Hirose, Tomoyasu

AU - Sugawara, Akihiro

AU - Kobayashi, Yoshinori

AU - Omura, Satoshi

AU - Sunazuka, Toshiaki

PY - 2013/8/28

Y1 - 2013/8/28

N2 - A first asymmetric total synthesis and determination of the absolute configuration of neoxaline has been accomplished through the highly stereoselective introduction of a reverse prenyl group to create a quaternary carbon stereocenter using (-)-3a-hydroxyfuroindoline as a building block, construction of the indoline spiroaminal via cautious stepwise oxidations with cyclizations from the indoline, assembly of (Z)-dehydrohistidine, and photoisomerization of unnatural (Z)-neoxaline to the natural (E)-neoxaline as the key steps.

AB - A first asymmetric total synthesis and determination of the absolute configuration of neoxaline has been accomplished through the highly stereoselective introduction of a reverse prenyl group to create a quaternary carbon stereocenter using (-)-3a-hydroxyfuroindoline as a building block, construction of the indoline spiroaminal via cautious stepwise oxidations with cyclizations from the indoline, assembly of (Z)-dehydrohistidine, and photoisomerization of unnatural (Z)-neoxaline to the natural (E)-neoxaline as the key steps.

UR - http://www.scopus.com/inward/record.url?scp=84883305859&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84883305859&partnerID=8YFLogxK

U2 - 10.1021/ja406657v

DO - 10.1021/ja406657v

M3 - Article

C2 - 23957424

AN - SCOPUS:84883305859

VL - 135

SP - 12568

EP - 12571

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

SN - 0002-7863

IS - 34

ER -