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

Eduard Dolušić; Laurent De Backer; Stéphane Collin; Steve Lanners

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

Eduard Dolušić, Laurent De Backer, Stéphane Collin, Steve Lanners

Research output: Contribution to conference › Poster › peer-review

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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 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.

Original language	English
Pages	Book of Abstracts, 14th Belgian Organic Synthesis Symposium, P087, p. 136
Number of pages	1
Publication status	Published - 13 Jul 2014
Event	BOSS XIV - 14th Belgian Organic Synthesis Symposium - Aula Magna, Louvain-la-Neuve, Belgium Duration: 13 Jul 2014 → 18 Jul 2014

Conference

Conference	BOSS XIV - 14th Belgian Organic Synthesis Symposium
Country/Territory	Belgium
City	Louvain-la-Neuve
Period	13/07/14 → 18/07/14

Access to Document

Dolusic poster LLN 2014Final published version, 2.32 MB

4 Poster
1 Abstract

Flow sinteza kombretastatina A-4
Translated title of the contribution: Flow synthesis of Combretastatin A-4Cazin, I., De Backer, L., Collin, S., Desrues, T., Dolusic, E. & Lanners, S., 22 Oct 2016.
Research output: Contribution to conference › Abstract

File
Flow synthesis of combretastatin A-4
Cazin, I., Dolusic, E. & Lanners, S. (Supervisor), 5 Nov 2016, p. 53 - HS P 17. 1 p.
Research output: Contribution to conference › Poster

Open Access
File
Z-Selective semi-hydrogenation of alkynes under continuous flow as part of an envisaged synthesis of combretastatin A-4
Dolušić, E., De Backer, L., Collin, S. & Lanners, S., 6 Jul 2014, p. Book of Abstracts, Balticum Organicum Syntheticum 2014, P016, p. 60. 1 p.
Research output: Contribution to conference › Poster › peer-review

Open Access
File

1 Finished

MICROECO: RW-Développement d'un procédé microfluide continu, à empreinte écologique minimale, pour la production de peroxyde d'hydrogène par synthèse directe
Lanners, S. (PI) & Dolušić, E. (CoI)
1/02/13 → 1/02/17
Project: Research

Physical Chemistry and characterization(PC2)
Wouters, J. (Manager), Aprile, C. (Manager) & Fusaro, L. (Manager)
Technological Platform Physical Chemistry and characterization
Facility/equipment: Technological Platform

3 Participation in conference
2 Participation to a Symposium, a study Day

Balticum Organicum Syntheticum 2014
Dolusic, E. (Poster)
6 Jul 2014 → 9 Jul 2014
Activity: Participating in or organising an event types › Participation in conference
BOSS XIV - 14th Belgian Organic Synthesis Symposium
Dolusic, E. (Poster)
13 Jul 2014 → 18 Jul 2014
Activity: Participating in or organising an event types › Participation in conference
Microfluidics: Fundamentals and Applications - BePCIS symposium
Dolusic, E. (Participant)
8 May 2014
Activity: Participating in or organising an event types › Participation to a Symposium, a study Day

Cite this

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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.",

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month = jul,

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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SELECTIVE SEMIREDUCTION OF ALKYNES AS PART OF AN ENVISAGED CONTINUOUS FLOW SYNTHESIS OF COMBRETASTATIN A-4. / Dolušić, Eduard; De Backer, Laurent; Collin, Stéphane et al.
2014. Book of Abstracts, 14th Belgian Organic Synthesis Symposium, P087, p. 136 Poster session presented at BOSS XIV - 14th Belgian Organic Synthesis Symposium, Louvain-la-Neuve, Belgium.

Research output: Contribution to conference › Poster › peer-review

TY - CONF

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.

M3 - Poster

SP - Book of Abstracts, 14th Belgian Organic Synthesis Symposium, P087, p. 136

T2 - BOSS XIV - 14th Belgian Organic Synthesis Symposium

Y2 - 13 July 2014 through 18 July 2014

ER -

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

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