SELECTIVE SEMIREDUCTION OF ALKYNES AS PART OF AN ENVISAGED CONTINUOUS FLOW 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 is endowed with 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, 14th Belgian Organic Synthesis Symposium, P087, p. 136
Nombre de pages1
étatPublié - 13 juil. 2014
EvénementBOSS XIV - 14th Belgian Organic Synthesis Symposium - Aula Magna, Louvain-la-Neuve, Belgique
Durée: 13 juil. 201418 juil. 2014

Une conférence

Une conférenceBOSS XIV - 14th Belgian Organic Synthesis Symposium
PaysBelgique
La villeLouvain-la-Neuve
période13/07/1418/07/14

Empreinte digitale

Alkynes
Derivatives
Stilbenes
Biological Products
Hydrogenation
fosbretabulin

Citer ceci

Dolušić, E., De Backer, L., Collin, S., & Lanners, S. (2014). SELECTIVE SEMIREDUCTION OF ALKYNES AS PART OF AN ENVISAGED CONTINUOUS FLOW SYNTHESIS OF COMBRETASTATIN A-4. Book of Abstracts, 14th Belgian Organic Synthesis Symposium, P087, p. 136. Poster présenté � BOSS XIV - 14th Belgian Organic Synthesis Symposium, Louvain-la-Neuve, Belgique.
Dolušić, Eduard ; De Backer, Laurent ; Collin, Stéphane ; Lanners, Steve. / SELECTIVE SEMIREDUCTION OF ALKYNES AS PART OF AN ENVISAGED CONTINUOUS FLOW SYNTHESIS OF COMBRETASTATIN A-4. Poster présenté � BOSS XIV - 14th Belgian Organic Synthesis Symposium, Louvain-la-Neuve, Belgique.1 p.
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title = "SELECTIVE SEMIREDUCTION OF ALKYNES AS PART OF AN ENVISAGED CONTINUOUS FLOW SYNTHESIS OF COMBRETASTATIN A-4",
abstract = "Combretastatin A-4 (1) is a natural product isolated from the South African bushwillow tree Combretum caffrum. It is endowed with 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 inflow, 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 = "13",
language = "English",
pages = "Book of Abstracts, 14th Belgian Organic Synthesis Symposium, P087, p. 136",
note = "BOSS XIV - 14th Belgian Organic Synthesis Symposium ; Conference date: 13-07-2014 Through 18-07-2014",

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Dolušić, E, De Backer, L, Collin, S & Lanners, S 2014, 'SELECTIVE SEMIREDUCTION OF ALKYNES AS PART OF AN ENVISAGED CONTINUOUS FLOW SYNTHESIS OF COMBRETASTATIN A-4', BOSS XIV - 14th Belgian Organic Synthesis Symposium, Louvain-la-Neuve, Belgique, 13/07/14 - 18/07/14 p. Book of Abstracts, 14th Belgian Organic Synthesis Symposium, P087, p. 136.

SELECTIVE SEMIREDUCTION OF ALKYNES AS PART OF AN ENVISAGED CONTINUOUS FLOW SYNTHESIS OF COMBRETASTATIN A-4. / Dolušić, Eduard; De Backer, Laurent; Collin, Stéphane; Lanners, Steve.

2014. Book of Abstracts, 14th Belgian Organic Synthesis Symposium, P087, p. 136 Poster présenté � BOSS XIV - 14th Belgian Organic Synthesis Symposium, Louvain-la-Neuve, Belgique.

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

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T1 - SELECTIVE SEMIREDUCTION OF ALKYNES AS PART OF AN ENVISAGED CONTINUOUS FLOW SYNTHESIS OF COMBRETASTATIN A-4

AU - Dolušić, Eduard

AU - De Backer, Laurent

AU - Collin, Stéphane

AU - Lanners, Steve

PY - 2014/7/13

Y1 - 2014/7/13

N2 - Combretastatin A-4 (1) is a natural product isolated from the South African bushwillow tree Combretum caffrum. It is endowed with 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 inflow, 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 is endowed with 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 inflow, 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.

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Dolušić E, De Backer L, Collin S, Lanners S. SELECTIVE SEMIREDUCTION OF ALKYNES AS PART OF AN ENVISAGED CONTINUOUS FLOW SYNTHESIS OF COMBRETASTATIN A-4. 2014. Poster présenté � BOSS XIV - 14th Belgian Organic Synthesis Symposium, Louvain-la-Neuve, Belgique.