Diels-Alder adducts derived from the natural phthalide Z-ligustilide

Erik Lager; Anders Sundin; Ruben A. Toscano; Guillermo Delgado; Olov Sterner

doi:10.1016/j.tetlet.2007.04.059

Diels-Alder adducts derived from the natural phthalide Z-ligustilide

Erik Lager, Anders Sundin, Ruben A. Toscano, Guillermo Delgado, Olov Sterner

Centre for Analysis and Synthesis

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

Abstract

Z-Ligustilide, a naturally occurring phthalide isolated from Ligusticum porteri, underwent Diels-Alder reactions with different dienophiles yielding novel tricyclic products with potentially interesting biological properties. Where selectivity was possible, the reactions performed showed regio- and stereoselectivity. The experimental results with ethyl acrylate were compared with the selectivity predicted by ab initio calculations.

Original language	English
Pages (from-to)	4215-4218
Journal	Tetrahedron Letters
Volume	48
Issue number	24
DOIs	https://doi.org/10.1016/j.tetlet.2007.04.059
Publication status	Published - 2007

Bibliographical note

The information about affiliations in this record was updated in December 2015.
The record was previously connected to the following departments: Organic chemistry (S/LTH) (011001240)

Subject classification (UKÄ)

Organic Chemistry

Free keywords

STAT3
Z-ligustilide
galiellalactone
ab initio
Diels-Alder

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10.1016/j.tetlet.2007.04.059

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title = "Diels-Alder adducts derived from the natural phthalide Z-ligustilide",

abstract = "Z-Ligustilide, a naturally occurring phthalide isolated from Ligusticum porteri, underwent Diels-Alder reactions with different dienophiles yielding novel tricyclic products with potentially interesting biological properties. Where selectivity was possible, the reactions performed showed regio- and stereoselectivity. The experimental results with ethyl acrylate were compared with the selectivity predicted by ab initio calculations.",

keywords = "STAT3, Z-ligustilide, galiellalactone, ab initio, Diels-Alder",

author = "Erik Lager and Anders Sundin and Toscano, {Ruben A.} and Guillermo Delgado and Olov Sterner",

note = "The information about affiliations in this record was updated in December 2015. The record was previously connected to the following departments: Organic chemistry (S/LTH) (011001240)",

year = "2007",

doi = "10.1016/j.tetlet.2007.04.059",

language = "English",

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journal = "Tetrahedron Letters",

issn = "0040-4039",

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T1 - Diels-Alder adducts derived from the natural phthalide Z-ligustilide

AU - Lager, Erik

AU - Sundin, Anders

AU - Toscano, Ruben A.

AU - Delgado, Guillermo

AU - Sterner, Olov

N1 - The information about affiliations in this record was updated in December 2015. The record was previously connected to the following departments: Organic chemistry (S/LTH) (011001240)

PY - 2007

Y1 - 2007

N2 - Z-Ligustilide, a naturally occurring phthalide isolated from Ligusticum porteri, underwent Diels-Alder reactions with different dienophiles yielding novel tricyclic products with potentially interesting biological properties. Where selectivity was possible, the reactions performed showed regio- and stereoselectivity. The experimental results with ethyl acrylate were compared with the selectivity predicted by ab initio calculations.

AB - Z-Ligustilide, a naturally occurring phthalide isolated from Ligusticum porteri, underwent Diels-Alder reactions with different dienophiles yielding novel tricyclic products with potentially interesting biological properties. Where selectivity was possible, the reactions performed showed regio- and stereoselectivity. The experimental results with ethyl acrylate were compared with the selectivity predicted by ab initio calculations.

KW - STAT3

KW - Z-ligustilide

KW - galiellalactone

KW - ab initio

KW - Diels-Alder

U2 - 10.1016/j.tetlet.2007.04.059

DO - 10.1016/j.tetlet.2007.04.059

M3 - Article

SN - 0040-4039

VL - 48

SP - 4215

EP - 4218

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 24

ER -

Diels-Alder adducts derived from the natural phthalide Z-ligustilide

Abstract

Bibliographical note

Subject classification (UKÄ)

Free keywords

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