A highly stereoselective intramolecular Diels-Alder reaction for construction of the AB ring moiety of bruceantin

Kenji Usui; Takahiro Suzuki; Masahisa Nakada

doi:10.1016/j.tetlet.2015.01.139

A highly stereoselective intramolecular Diels-Alder reaction for construction of the AB ring moiety of bruceantin

Kenji Usui, Takahiro Suzuki, Masahisa Nakada^*

^*この研究の対応する著者

先進理工学部

研究成果: Article › 査読

10 被引用数 (Scopus)

抄録

A highly stereoselective intramolecular Diels-Alder (IMDA) reaction for the construction of the AB ring moiety of bruceantin is described. The product of the IMDA reaction comprises a trans-AB ring junction and stereotetrad including an all carbon quaternary stereogenic center, wherein three stereogenic centers correspond to those of bruceantin. Functional groups embedded in the product are suitable for a variety of transformations. Hence, this IMDA product could be a useful intermediate for the enantioselective total synthesis of not only bruceantin, but also other bioactive compounds.

本文言語	English
ページ（範囲）	1247-1251
ページ数	5
ジャーナル	Tetrahedron Letters
巻	56
号	10
DOI	https://doi.org/10.1016/j.tetlet.2015.01.139
出版ステータス	Published - 2015 3月 4

ASJC Scopus subject areas

生化学
創薬
有機化学

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10.1016/j.tetlet.2015.01.139

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title = "A highly stereoselective intramolecular Diels-Alder reaction for construction of the AB ring moiety of bruceantin",

abstract = "A highly stereoselective intramolecular Diels-Alder (IMDA) reaction for the construction of the AB ring moiety of bruceantin is described. The product of the IMDA reaction comprises a trans-AB ring junction and stereotetrad including an all carbon quaternary stereogenic center, wherein three stereogenic centers correspond to those of bruceantin. Functional groups embedded in the product are suitable for a variety of transformations. Hence, this IMDA product could be a useful intermediate for the enantioselective total synthesis of not only bruceantin, but also other bioactive compounds.",

keywords = "Diels-Alder reaction, Intramolecular, Natural product, Stereoselective, Synthesis",

author = "Kenji Usui and Takahiro Suzuki and Masahisa Nakada",

note = "Funding Information: This work was financially supported in part by the Grant-in-Aid for Scientific Research (B) ( 25293003 ) by MEXT – Japan, and a Waseda University Grant for Special Research Projects. Publisher Copyright: {\textcopyright} 2015 Elsevier Ltd. All rights reserved.",

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AU - Usui, Kenji

AU - Suzuki, Takahiro

AU - Nakada, Masahisa

N1 - Funding Information: This work was financially supported in part by the Grant-in-Aid for Scientific Research (B) ( 25293003 ) by MEXT – Japan, and a Waseda University Grant for Special Research Projects. Publisher Copyright: © 2015 Elsevier Ltd. All rights reserved.

PY - 2015/3/4

Y1 - 2015/3/4

N2 - A highly stereoselective intramolecular Diels-Alder (IMDA) reaction for the construction of the AB ring moiety of bruceantin is described. The product of the IMDA reaction comprises a trans-AB ring junction and stereotetrad including an all carbon quaternary stereogenic center, wherein three stereogenic centers correspond to those of bruceantin. Functional groups embedded in the product are suitable for a variety of transformations. Hence, this IMDA product could be a useful intermediate for the enantioselective total synthesis of not only bruceantin, but also other bioactive compounds.

AB - A highly stereoselective intramolecular Diels-Alder (IMDA) reaction for the construction of the AB ring moiety of bruceantin is described. The product of the IMDA reaction comprises a trans-AB ring junction and stereotetrad including an all carbon quaternary stereogenic center, wherein three stereogenic centers correspond to those of bruceantin. Functional groups embedded in the product are suitable for a variety of transformations. Hence, this IMDA product could be a useful intermediate for the enantioselective total synthesis of not only bruceantin, but also other bioactive compounds.

KW - Diels-Alder reaction

KW - Intramolecular

KW - Natural product

KW - Stereoselective

KW - Synthesis

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A highly stereoselective intramolecular Diels-Alder reaction for construction of the AB ring moiety of bruceantin

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