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

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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 languageEnglish
PagesBook of Abstracts, 14th Belgian Organic Synthesis Symposium, P087, p. 136
Number of pages1
Publication statusPublished - 13 Jul 2014
EventBOSS XIV - 14th Belgian Organic Synthesis Symposium - Aula Magna, Louvain-la-Neuve, Belgium
Duration: 13 Jul 201418 Jul 2014

Conference

ConferenceBOSS XIV - 14th Belgian Organic Synthesis Symposium
CountryBelgium
CityLouvain-la-Neuve
Period13/07/1418/07/14

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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. 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.