Research on Liebeskind-Srogl coupling/intramolecular Diels-Alder reaction cascade

Tomohiro Fujii; Yuta Oki; Masahisa Nakada

doi:10.1016/j.tetlet.2018.01.046

Research on Liebeskind-Srogl coupling/intramolecular Diels-Alder reaction cascade

Tomohiro Fujii, Yuta Oki, Masahisa Nakada^*

^*Corresponding author for this work

School of Advanced Science and Engineering

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

3 Citations (Scopus)

Abstract

The Liebeskind-Srogl coupling/intramolecular Diels-Alder (IMDA) reaction cascade that stereoselectively affords a tricarbocyclic compound with a trans–trans-cis fused ring system including an all-carbon quaternary stereogenic center at the ring junction is described. The cascade reactions proceed quickly and stereoselectively afford the products within 2 h at room temperature in the presence of a suitable thioester. The developed protocol as well as the prepared chiral compounds are useful for the enantioselective total synthesis of terpenoids with the trans–trans-cis fused ring system.

Original language	English
Pages (from-to)	882-886
Number of pages	5
Journal	Tetrahedron Letters
Volume	59
Issue number	10
DOIs	https://doi.org/10.1016/j.tetlet.2018.01.046
Publication status	Published - 2018 Mar 7

Keywords

Cascade
Diels-Alder
Intramolecular
Liebeskind-Srogl
Stereoselective

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2018.01.046

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title = "Research on Liebeskind-Srogl coupling/intramolecular Diels-Alder reaction cascade",

abstract = "The Liebeskind-Srogl coupling/intramolecular Diels-Alder (IMDA) reaction cascade that stereoselectively affords a tricarbocyclic compound with a trans–trans-cis fused ring system including an all-carbon quaternary stereogenic center at the ring junction is described. The cascade reactions proceed quickly and stereoselectively afford the products within 2 h at room temperature in the presence of a suitable thioester. The developed protocol as well as the prepared chiral compounds are useful for the enantioselective total synthesis of terpenoids with the trans–trans-cis fused ring system.",

keywords = "Cascade, Diels-Alder, Intramolecular, Liebeskind-Srogl, Stereoselective",

author = "Tomohiro Fujii and Yuta Oki and Masahisa Nakada",

note = "Funding Information: We acknowledge supports of the Materials Characterization Central Laboratory, Waseda University – Japan, for characterization of new compounds. This work was financially supported in part by the Grant-in-Aid for Scientific Research on Innovative Areas 2707 Middle molecular strategy from MEXT – Japan and a Waseda University Grant for Special Research Projects. Publisher Copyright: {\textcopyright} 2018 Elsevier Ltd",

year = "2018",

month = mar,

day = "7",

doi = "10.1016/j.tetlet.2018.01.046",

language = "English",

volume = "59",

pages = "882--886",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Limited",

number = "10",

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T1 - Research on Liebeskind-Srogl coupling/intramolecular Diels-Alder reaction cascade

AU - Fujii, Tomohiro

AU - Oki, Yuta

AU - Nakada, Masahisa

N1 - Funding Information: We acknowledge supports of the Materials Characterization Central Laboratory, Waseda University – Japan, for characterization of new compounds. This work was financially supported in part by the Grant-in-Aid for Scientific Research on Innovative Areas 2707 Middle molecular strategy from MEXT – Japan and a Waseda University Grant for Special Research Projects. Publisher Copyright: © 2018 Elsevier Ltd

PY - 2018/3/7

Y1 - 2018/3/7

N2 - The Liebeskind-Srogl coupling/intramolecular Diels-Alder (IMDA) reaction cascade that stereoselectively affords a tricarbocyclic compound with a trans–trans-cis fused ring system including an all-carbon quaternary stereogenic center at the ring junction is described. The cascade reactions proceed quickly and stereoselectively afford the products within 2 h at room temperature in the presence of a suitable thioester. The developed protocol as well as the prepared chiral compounds are useful for the enantioselective total synthesis of terpenoids with the trans–trans-cis fused ring system.

AB - The Liebeskind-Srogl coupling/intramolecular Diels-Alder (IMDA) reaction cascade that stereoselectively affords a tricarbocyclic compound with a trans–trans-cis fused ring system including an all-carbon quaternary stereogenic center at the ring junction is described. The cascade reactions proceed quickly and stereoselectively afford the products within 2 h at room temperature in the presence of a suitable thioester. The developed protocol as well as the prepared chiral compounds are useful for the enantioselective total synthesis of terpenoids with the trans–trans-cis fused ring system.

KW - Cascade

KW - Diels-Alder

KW - Intramolecular

KW - Liebeskind-Srogl

KW - Stereoselective

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DO - 10.1016/j.tetlet.2018.01.046

M3 - Article

AN - SCOPUS:85041286518

SN - 0040-4039

VL - 59

SP - 882

EP - 886

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 10

ER -

Research on Liebeskind-Srogl coupling/intramolecular Diels-Alder reaction cascade

Abstract

Keywords

ASJC Scopus subject areas

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