Projects per year
Abstract
Combretastatin A-4 (1) is a natural product isolated from the South African bushwillow tree Combretum caffrum and endowed with a powerful inhibitory activity on microtubule formation as well as a related antiangiogenic activity.1-3 As such, 1 has a strong potential in the anticancer therapy. A lot of effort has been done on the development of new derivatives of this compound, in order to improve the properties such as solubility and stability and to understand the structure-activity relationships around this series.4-7 Our group has recently turned its attention to developing a synthetic procedure for combretastatin A-4 performed entirely in flow, which should enable continuous production of this useful compound and its derivatives in significant quantities. The full results of this work will be presented in due course.
A crucial step in this synthetic strategy is a selective semi-reduction of the triple bond of an alkyne precursor to the Z-double bond present in the final product. The Lindlar-type hydrogenation in flow has been described only scarcely and for products more stable than Z-stilbenes.8 We therefore set out to explore the applicability of this technique within our synthetic procedure and also decided to expand it to a wider range of structurally various alkynes. The experimental conditions have been varied according to the general scheme below and the - rather promising - results are shown in the poster.
A crucial step in this synthetic strategy is a selective semi-reduction of the triple bond of an alkyne precursor to the Z-double bond present in the final product. The Lindlar-type hydrogenation in flow has been described only scarcely and for products more stable than Z-stilbenes.8 We therefore set out to explore the applicability of this technique within our synthetic procedure and also decided to expand it to a wider range of structurally various alkynes. The experimental conditions have been varied according to the general scheme below and the - rather promising - results are shown in the poster.
Original language | English |
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Publication status | Published - 16 Oct 2013 |
Event | FROST4 - 4th Conference on Frontiers in Organic Synthesis Technology - Budapest, Hungary Duration: 16 Oct 2013 → 18 Oct 2013 |
Conference
Conference | FROST4 - 4th Conference on Frontiers in Organic Synthesis Technology |
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Country | Hungary |
City | Budapest |
Period | 16/10/13 → 18/10/13 |
Keywords
- Lindlar reduction, combretastatin A-4
Fingerprint Dive into the research topics of 'Partial alkyne reduction in flow: Adaptation of the lindlar protocol prompted by a flow synthesis of combretastatin A-4'. Together they form a unique fingerprint.
Projects
- 1 Finished
Equipment
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Physical Chemistry and characterization(PC2)
Johan Wouters (Manager) & Carmela Aprile (Manager)
Technological Platform Physical Chemistry and characterizationFacility/equipment: Technological Platform
Activities
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BOSS XIV - 14th Belgian Organic Synthesis Symposium
Eduard Dolusic (Poster)
13 Jul 2014 → 18 Jul 2014Activity: Participating in or organising an event types › Participation in conference
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Balticum Organicum Syntheticum 2014
Eduard Dolusic (Poster)
6 Jul 2014 → 9 Jul 2014Activity: Participating in or organising an event types › Participation in conference
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Microfluidics: Fundamentals and Applications - BePCIS symposium
Eduard Dolusic (Participant)
8 May 2014Activity: Participating in or organising an event types › Participation to a Symposium, a study Day