Z-Selective semi-hydrogenation of alkynes under continuous flow as part of an envisaged 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 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.
Original languageEnglish
PagesBook of Abstracts, Balticum Organicum Syntheticum 2014, P016, p. 60
Number of pages1
Publication statusPublished - 6 Jul 2014
EventBalticum Organicum Syntheticum 2014 - Vilnius, Lithuania
Duration: 6 Jul 20149 Jul 2014

Conference

ConferenceBalticum Organicum Syntheticum 2014
CountryLithuania
CityVilnius
Period6/07/149/07/14

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