C - Chemistry – Metallurgy – 07 – C
Patent
C - Chemistry, Metallurgy
07
C
C07C 41/30 (2006.01) C07C 43/23 (2006.01)
Patent
CA 2432592
The present invention relates materials and methods for synthesizing stilbenes, and in particular to processes for the synthesis of substituted stilbenes such as combretastatin A4. The present invention relates in particular to methods which are stereoselective for either the cis or the trans isomer of the substituted stilbene, using a Perkin-type condensation of an arylacetic acid and a substituted benzaldehyde, followed by a decarboxylation reaction to produce the substituted cis-stilbenes or a Suzuki- type reaction involving a Z or E-ethenyl halide and a substituted boronic acid in the presence of a palladium catalyst to produce specifically either the Z or E-isomer of substituted stilbenes.
L'invention porte sur des substances et des méthodes de synthèse de stilbènes, plus précisément à des procédés de synthèse de stilbènes substituées, telles que la combretastatine A4. Cette invention concerne plus particulièrement des méthodes stéréosélectives de l'isomère cis ou trans de la stilbène substituée, utilisant une condensation de type Perkin d'un acide aryalectique et d'un benzaldehyde substitué, suivie d'une réaction de décarboxylation permettant de fabriquer les stilbènes-cis substituées ou une réaction de type Suzuki contenant un halyde ethenyle <I>Z</I> ou <I>E</I> et un acide boronique substitué en présence d'un catalyseur de palladium afin de fabriquer précisément l'isomère Z ou E des stilbènes substituées.
Gaukroger Keira
Hadfield John Anthony
Hepworth Lucy Annette
Lawrence Nicholas James
Mcgown Alan Thomson
Bereskin & Parr
Cancer Research Technology Limited
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