Homo- and heterogeneous Ru-based metathesis catalysts in cross-metathesis of 15-allylestrone-towards 17β-hydroxysteroid dehydrogenase type 1 inhibitors

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  • SOLVAY GmbH
  • Instytut Chemii Bioorganicznej Polskiej Akademii Nauk
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Original languageEnglish
Pages (from-to)3019-3022
Number of pages4
JournalTetrahedron Letters
Volume49
Issue number18
Publication statusPublished - 29 Feb 2008

Abstract

The cross-metathesis of allylestrone with acrylic acid derivatives using homogeneous and heterogenized Ru-catalysts was evaluated for the synthesis of a new 17β-hydroxysteroid dehydrogenase type 1 inhibitor. Hoveyda-type catalyst containing an additional diethylamino group turned out to be comparably active as homogeneous Grubbs II catalyst after immobilization on an acidic ion exchange resin which greatly facilitated workup.

Keywords

    Catalysis, Cross-olefin metathesis, Enzyme inhibitor, Immobilization, Ru-catalyst, Steroids

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Cite this

Homo- and heterogeneous Ru-based metathesis catalysts in cross-metathesis of 15-allylestrone-towards 17β-hydroxysteroid dehydrogenase type 1 inhibitors. / Kirschning, Andreas; Harmrolfs, Kirsten; Mennecke, Klaas et al.
In: Tetrahedron Letters, Vol. 49, No. 18, 29.02.2008, p. 3019-3022.

Research output: Contribution to journalArticleResearchpeer review

Kirschning A, Harmrolfs K, Mennecke K, Messinger J, Schön U, Grela K. Homo- and heterogeneous Ru-based metathesis catalysts in cross-metathesis of 15-allylestrone-towards 17β-hydroxysteroid dehydrogenase type 1 inhibitors. Tetrahedron Letters. 2008 Feb 29;49(18):3019-3022. doi: 10.1016/j.tetlet.2008.02.134
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abstract = "The cross-metathesis of allylestrone with acrylic acid derivatives using homogeneous and heterogenized Ru-catalysts was evaluated for the synthesis of a new 17β-hydroxysteroid dehydrogenase type 1 inhibitor. Hoveyda-type catalyst containing an additional diethylamino group turned out to be comparably active as homogeneous Grubbs II catalyst after immobilization on an acidic ion exchange resin which greatly facilitated workup.",
keywords = "Catalysis, Cross-olefin metathesis, Enzyme inhibitor, Immobilization, Ru-catalyst, Steroids",
author = "Andreas Kirschning and Kirsten Harmrolfs and Klaas Mennecke and Josef Messinger and Uwe Sch{\"o}n and Karol Grela",
note = "Funding information: The work was funded by the Deutsche Forschungsgemeinschaft—Polisch Academy of Sciences joint project {\textquoteleft}Synthetische Nutzung von immobilisierten Ruthenium–Carben–Katalysatoren in Durchflussmikroreaktoren{\textquoteright} (436 POL 113/109/0-1) and the Fonds der Chemischen Industrie.",
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TY - JOUR

T1 - Homo- and heterogeneous Ru-based metathesis catalysts in cross-metathesis of 15-allylestrone-towards 17β-hydroxysteroid dehydrogenase type 1 inhibitors

AU - Kirschning, Andreas

AU - Harmrolfs, Kirsten

AU - Mennecke, Klaas

AU - Messinger, Josef

AU - Schön, Uwe

AU - Grela, Karol

N1 - Funding information: The work was funded by the Deutsche Forschungsgemeinschaft—Polisch Academy of Sciences joint project ‘Synthetische Nutzung von immobilisierten Ruthenium–Carben–Katalysatoren in Durchflussmikroreaktoren’ (436 POL 113/109/0-1) and the Fonds der Chemischen Industrie.

PY - 2008/2/29

Y1 - 2008/2/29

N2 - The cross-metathesis of allylestrone with acrylic acid derivatives using homogeneous and heterogenized Ru-catalysts was evaluated for the synthesis of a new 17β-hydroxysteroid dehydrogenase type 1 inhibitor. Hoveyda-type catalyst containing an additional diethylamino group turned out to be comparably active as homogeneous Grubbs II catalyst after immobilization on an acidic ion exchange resin which greatly facilitated workup.

AB - The cross-metathesis of allylestrone with acrylic acid derivatives using homogeneous and heterogenized Ru-catalysts was evaluated for the synthesis of a new 17β-hydroxysteroid dehydrogenase type 1 inhibitor. Hoveyda-type catalyst containing an additional diethylamino group turned out to be comparably active as homogeneous Grubbs II catalyst after immobilization on an acidic ion exchange resin which greatly facilitated workup.

KW - Catalysis

KW - Cross-olefin metathesis

KW - Enzyme inhibitor

KW - Immobilization

KW - Ru-catalyst

KW - Steroids

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U2 - 10.1016/j.tetlet.2008.02.134

DO - 10.1016/j.tetlet.2008.02.134

M3 - Article

AN - SCOPUS:41349097890

VL - 49

SP - 3019

EP - 3022

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 18

ER -

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