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

Research output: Contribution to journal › Article › peer-review

28 Citations (Scopus)

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.

Original language	English
Pages (from-to)	12568-12571
Number of pages	4
Journal	Journal of the American Chemical Society
Volume	135
Issue number	34
DOIs	https://doi.org/10.1021/ja406657v
Publication status	Published - 2013 Aug 28
Externally published	Yes

ASJC Scopus subject areas

Catalysis
Chemistry(all)
Biochemistry
Colloid and Surface Chemistry

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10.1021/ja406657v

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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",

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language = "English",

volume = "135",

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journal = "Journal of the American Chemical Society",

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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.

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