Z-Selective semi-hydrogenation of alkynes under continuous flow as part of an envisaged synthesis of combretastatin A-4

Résultats de recherche: Contribution à un événement scientifique (non publié)Poster

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Résumé

Combretastatin A-4 (1) is a natural product isolated from the South African bushwillow tree Combretum caffrum. It has a powerful inhibitory activity on microtubule formation as well as a related antiangiogenic activity.[1-2] As such, 1 has a strong potential in the anticancer therapy, prompting the development of new derivatives.[3-6] We have turned our attention to the design of a synthetic procedure for 1 performed entirely in flow, which should enable continuous and rapid production of this useful compound and its derivatives in significant quantities.
Presented in this poster is a crucial step in this synthetic strategy - a selective semi-reduction of the triple bond of an alkyne precursor to the Z-double bond in the final product. The Lindlar-type hydrogenation in flow has been described only scarcely and for products typically more stable than Z-stilbenes.[7] We therefore set out to explore this technique and decided to expand it to a wider range of structurally various alkynes.
langue originaleAnglais
PagesBook of Abstracts, Balticum Organicum Syntheticum 2014, P016, p. 60
Nombre de pages1
étatPublié - 6 juil. 2014
EvénementBalticum Organicum Syntheticum 2014 - Vilnius, Lituanie
Durée: 6 juil. 20149 juil. 2014

Une conférence

Une conférenceBalticum Organicum Syntheticum 2014
PaysLituanie
La villeVilnius
période6/07/149/07/14

Empreinte digitale

Alkynes
Hydrogenation
Derivatives
Stilbenes
Biological Products
fosbretabulin

Citer ceci

Dolušić, E., De Backer, L., Collin, S., & Lanners, S. (2014). Z-Selective semi-hydrogenation of alkynes under continuous flow as part of an envisaged synthesis of combretastatin A-4. Book of Abstracts, Balticum Organicum Syntheticum 2014, P016, p. 60. Poster présenté � Balticum Organicum Syntheticum 2014, Vilnius, Lituanie.
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abstract = "Combretastatin A-4 (1) is a natural product isolated from the South African bushwillow tree Combretum caffrum. It has a powerful inhibitory activity on microtubule formation as well as a related antiangiogenic activity.[1-2] As such, 1 has a strong potential in the anticancer therapy, prompting the development of new derivatives.[3-6] We have turned our attention to the design of a synthetic procedure for 1 performed entirely in flow, which should enable continuous and rapid production of this useful compound and its derivatives in significant quantities. Presented in this poster is a crucial step in this synthetic strategy - a selective semi-reduction of the triple bond of an alkyne precursor to the Z-double bond in the final product. The Lindlar-type hydrogenation in flow has been described only scarcely and for products typically more stable than Z-stilbenes.[7] We therefore set out to explore this technique and decided to expand it to a wider range of structurally various alkynes.",
author = "Eduard Dolušić and {De Backer}, Laurent and St{\'e}phane Collin and Steve Lanners",
year = "2014",
month = "7",
day = "6",
language = "English",
pages = "Book of Abstracts, Balticum Organicum Syntheticum 2014, P016, p. 60",
note = "Balticum Organicum Syntheticum 2014 ; Conference date: 06-07-2014 Through 09-07-2014",

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Dolušić, E, De Backer, L, Collin, S & Lanners, S 2014, 'Z-Selective semi-hydrogenation of alkynes under continuous flow as part of an envisaged synthesis of combretastatin A-4', Balticum Organicum Syntheticum 2014, Vilnius, Lituanie, 6/07/14 - 9/07/14 p. Book of Abstracts, Balticum Organicum Syntheticum 2014, P016, p. 60.

Z-Selective semi-hydrogenation of alkynes under continuous flow as part of an envisaged synthesis of combretastatin A-4. / Dolušić, Eduard; De Backer, Laurent; Collin, Stéphane; Lanners, Steve.

2014. Book of Abstracts, Balticum Organicum Syntheticum 2014, P016, p. 60 Poster présenté � Balticum Organicum Syntheticum 2014, Vilnius, Lituanie.

Résultats de recherche: Contribution à un événement scientifique (non publié)Poster

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T1 - Z-Selective semi-hydrogenation of alkynes under continuous flow as part of an envisaged synthesis of combretastatin A-4

AU - Dolušić, Eduard

AU - De Backer, Laurent

AU - Collin, Stéphane

AU - Lanners, Steve

PY - 2014/7/6

Y1 - 2014/7/6

N2 - Combretastatin A-4 (1) is a natural product isolated from the South African bushwillow tree Combretum caffrum. It has a powerful inhibitory activity on microtubule formation as well as a related antiangiogenic activity.[1-2] As such, 1 has a strong potential in the anticancer therapy, prompting the development of new derivatives.[3-6] We have turned our attention to the design of a synthetic procedure for 1 performed entirely in flow, which should enable continuous and rapid production of this useful compound and its derivatives in significant quantities. Presented in this poster is a crucial step in this synthetic strategy - a selective semi-reduction of the triple bond of an alkyne precursor to the Z-double bond in the final product. The Lindlar-type hydrogenation in flow has been described only scarcely and for products typically more stable than Z-stilbenes.[7] We therefore set out to explore this technique and decided to expand it to a wider range of structurally various alkynes.

AB - Combretastatin A-4 (1) is a natural product isolated from the South African bushwillow tree Combretum caffrum. It has a powerful inhibitory activity on microtubule formation as well as a related antiangiogenic activity.[1-2] As such, 1 has a strong potential in the anticancer therapy, prompting the development of new derivatives.[3-6] We have turned our attention to the design of a synthetic procedure for 1 performed entirely in flow, which should enable continuous and rapid production of this useful compound and its derivatives in significant quantities. Presented in this poster is a crucial step in this synthetic strategy - a selective semi-reduction of the triple bond of an alkyne precursor to the Z-double bond in the final product. The Lindlar-type hydrogenation in flow has been described only scarcely and for products typically more stable than Z-stilbenes.[7] We therefore set out to explore this technique and decided to expand it to a wider range of structurally various alkynes.

M3 - Poster

SP - Book of Abstracts, Balticum Organicum Syntheticum 2014, P016, p. 60

ER -