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^*

^*Corresponding author for this work

School of Advanced Science and Engineering

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

10 Citations (Scopus)

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.

Original language	English
Pages (from-to)	1247-1251
Number of pages	5
Journal	Tetrahedron Letters
Volume	56
Issue number	10
DOIs	https://doi.org/10.1016/j.tetlet.2015.01.139
Publication status	Published - 2015 Mar 4

Keywords

Diels-Alder reaction
Intramolecular
Natural product
Stereoselective
Synthesis

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

Access to Document

10.1016/j.tetlet.2015.01.139

Cite this

@article{ce2c7484639e48bd9bbc3907562e91eb,

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.",

year = "2015",

month = mar,

day = "4",

doi = "10.1016/j.tetlet.2015.01.139",

language = "English",

volume = "56",

pages = "1247--1251",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Limited",

number = "10",

}

TY - JOUR

T1 - A highly stereoselective intramolecular Diels-Alder reaction for construction of the AB ring moiety of bruceantin

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

UR - http://www.scopus.com/inward/record.url?scp=84923094344&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84923094344&partnerID=8YFLogxK

U2 - 10.1016/j.tetlet.2015.01.139

DO - 10.1016/j.tetlet.2015.01.139

M3 - Article

AN - SCOPUS:84923094344

SN - 0040-4039

VL - 56

SP - 1247

EP - 1251

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 10

ER -

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

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this